2024
296. Weeda, E. P.; Holland, C. M.; de Bueren, J. B.; Yuan, Z.; Alherech, M.; Coplien, J.; Haak, D.; Hegg, E. L.; Luterbacher, J.; Root, T. W.; Stahl, S. S. O2-Permeable Membrane Reactor for Continuous Oxidative Depolymerization of Lignin. Joule. 2024. DOI: 10.1016/j.joule.2024.08.015.
295. Su, Z.-M.; Deng, R.; Stahl, S. S. Zinc and Manganese Redox Potentials in Organic Solvents and their Influence on Nickel-Catalysed Cross-Electrophile Coupling. Nat. Chem. 2024. DOI: 10.1038/s41557-024-01627-5. Preprint.
294. Hoque, M. A.; Jiang, T.; Poole, D. L.; Stahl, S. S. Manganese-Mediated Electrochemical Oxidation of Thioethers to Sulfoxides Using Water as the Source of Oxygen Atoms. J. Am. Chem. Soc. 2024, 146, 21960-21967. DOI: 10.1021/jacs.4c07058. Preprint.
293. Subbotina, E.; Stahl, S. S.; Anastas, P.; Samec, J. S. M. Approaches to the Oxidative Deploymerization of Lignin. Lignin Chemistry: Characterization, Isolation, and Valorization [Online]; Liao, Y.; Sels, B. F., Eds; Wiley-VCH GmbH, 2024, 231-263. https://onlinelibrary.wiley.com/doi/10.1002/9783527839865.ch9
292. Khamespanah, F.; Gerken, J. B.; Mannel, D. S.; Nagy, S.; Kimmich, B.; Stahl, S. S. Nickel-Catalyzed Hydrocarboxylation of Terminal Unactivated Alkenes: Formation of Branched Carboxylic Acid and Competing Catalyst Deactivation from CO2 Reduction to CO. Organometallics. 2024, 43, 1502-1510. DOI: 10.1021/acs.organomet.4c00218. Preprint.
291. Cui, Y.; Weeda, E. P.; Omolabake, S.; Karlen, S. D.; Holland C. M.; Stahl, S. S. Oxidative Catalytic Fractionation of Lignocellulosic Biomass Using a Co-N-P-C Catalyst and One-Step Isolation of Aromatic Monomers via Centrifugal Partition Chromatography. ACS Sustainable Chem. Eng. 2024, 12, 9795-9804. DOI: 10.1021/acssuchemeng.4c02120. Preprint.
290. Hanneman, C. M.; Twilton, J.; Hall, M. N.; Goodwin, N. C.; Elward, J. M.; Lynch-Colameta, T.; Stahl S. S. Copper-Nitroxyl-Catalyzed α-Oxygenation of Cyclic Secondary Amines Including Application to Late-Stage Functionalization. J. Am. Chem. Soc. 2024, 146, 14439-14444. DOI: 10.1021/jacs.4c04359. Preprint.
289. Hall, M. N.; Lee, M.; Root, T. W.; Davies, H. M. L.; Stahl S. S. Heterogeneous Fe-N-C Catalyst for Aerobic Dehydrogenation of Hydrazones to Diazo Compounds Used for Carbene Transfer. J. Am. Chem. Soc. 2024, 146, 13741-13747. DOI: 10.1021/jacs.4c04430. Preprint.
288. Golden, D. L; Flynn, K. M.; Aikonen, S.; Hanneman, C. M.; Kalyani, D.; Krska, S. W.; Paton, R. S.; Stahl S. S. Radical chlorination of non-resonant heterobenzylic C-H bond and high-throughtput diversification of heterocycles. Chem. 2024, 5, 1593-1605. DOI: 10.1016/j.chempr.2024.04.001
287. Omolabake, S.; Holland, C.; Dulger, D. N.; Yuan, Z.; Hegg, E. L.; Hodge, D. B.; Stahl, S. S. Recovery of p-Hydroxybenzoic Acid from Cu-Catalyzed Alkaline Hydrogen Peroxide Pretreatment of Hybrid Poplar. ACS Sustainable Chem. Eng. 2024, 12, 5726-5730. DOI: 10.1021/acssuschemeng.3c08032. Preprint.
286. Dulger, D. N.; Yuan, Z.; Singh, S. K.; Omolabake, S.; Czarnecki, C. R.; Nikafshar, S.; Li, M.; Becsy-Jakab, V. E.; Park, S.; Park, S.; Nejad, M.; Stahl, S. S.; Hegg, E. L.; Hodge, D. B. Scale-Up of a Two-Stage Cu-Catalyzed Alkaline-Oxidative Pretreatment of Hybrid Poplar. Ind. Eng. Chem. Res. 2024, 63, 6182-6193. DOI: 10.1021/acs.iecr.3c04466. Preprint.
285. Palumbo, C. T.; Gu, N. X.; Bleem, A. C.; Sullivan, K. P.; Katahira, R.; Stanley, L. M.; Kenny, J. K.; Ingraham, M. A.; Ramirez, K. J.; Haugen, S. J.; Amendola, C. R.; Stahl, S. S.; Beckham, G. T. Catalytic carbon-carbon bond cleavage in lignin via manganese-zirconium-mediated autoxidation. Nat. Commun. 2024, 15. DOI: 10.1038/s41467-024-45038-z. Preprint.284. King, D. S.; Wang, F.; Gerken, J. B.; Gaggioli, C. A.; Guzei, I. A.; Kim, Y. J.; Stahl, S. S.; Gagliardi, L. Divergent Bimetallic Mechanisms in Copper(II)-Mediated C-C, N-N, and O-O Oxidative Coupling Reactions. J. Am. Chem. Soc. 2024, 146, 3521-3530. DOI: 10.1021/jacs.3c13649. Preprint.
283. Hoque, M. A.; Gerken, J. B.; Stahl, S. S. Synthetic dioxygenase reactivity by pairing electro-chemical oxygen reduction and water oxidation. Science 2024, 383, 173-178. DOI: 10.1126/science.adk5097. Preprint.
282. Mandal, M.; Buss, J. A.; Chen, S.-J.; Cramer, C. J.; Stahl, S. S. Mechanistic insights into radical formation and functionalization in copper/N-fluorobenzenesulfonimide radical-relay reactions. Chem. Sci. 2024, 15, 1364-1373. DOI: 10.1039/D3SC03597B. Preprint.
281. Rafiee, M.; Abrams, D. J.; Cardinale, L.; Goss, Z.; Romero-Arenas, A.; Stahl, S. S. Cyclic Voltammetry and Chronoamperometry: Mechanistic Tools for Organic Electrosynthesis. Chem. Soc. Rev. 2024, 53, 566-585. DOI: 10.1039/D2CS00706A. Preprint.
280. Gerken, J. B.; Stamoulis, A.; MacDonnell, M. L.; Stahl, S. S. Rate Equations for Reversible Disproportionation Reactions and Fitting to Time-Course Data. J. Phys. Chem. A. 2024, 128, 328-332. DOI: 10.1021/acs.jpca.3c05232. Preprint.
2023
279. Chen, S.-J.; Krska, S. W.; Stahl, S. S. Copper-Catalyzed Benzylic C-H Cross-Coupling Enabled by Redox Buffer: Expanding Synthetic Access to Three-Dimensional Chemical Space. Acc. Chem. Res. 2023. 56, 3604-3615. DOI: 10.1021/acs.accounts.3c00580. Preprint.
278. Gu, N. X.; Palumbo, C. T.; Bleem, A. C.; Sullivan, K. P.; Haugen S. J.; Woodworth, S. P.; Ramirez, K. J.; Kenny, J. K.; Stanley, L. D.; Katahira, R.; Stahl, S. S.; Beckham, G. T. Autoxidation Catalysis for Carbon-Carbon Bond Cleavage in Lignin. ACS. Cent. Sci. 2023, 9, 2277-2285. DOI: 10.1021/acscentsci.3c00813. Preprint.
277. Bates, J. S.; Martinez, J. J.; Hall, M. N.; Al-Omari, A. A.; Murphy, E.; Zeng, Y.; Luo, F.; Primbs, M.; Menga, D.; Bibent, N.; Sougrati, M.T.; Wagner, F. E.; Atanassov, P.; Wu, G.; Strasser, P.; Fellinger, T-P.; Jaouen, F.; Root, T. W.; Stahl, S. S. Chemical Kinetic Method for Active-Site Quantification in Fe-N-C Catalysts and Correlation with Molecular Probe and Spectroscopic Site-Counting Methods. J. Am. Chem. Soc. 2023, 145, 26222-26237. DOI: 10.1021/jacs.3c08790. Preprint.
276. Cardinale, L.; Stahl, S. S.; Kalyani, D.; Lehnherr, D. Overview of Outer-sphere Electron Transfer Mediators for Electrosynthesis. Adv. Catal. 2023, 27, 57-102. DOI:10.1016/bs.acat.2023.07.009. Preprint.
275. Maity, S.; Lopez, M. A.; Bates, D. M.; Lin, S.; Krska, S. W.; Stahl, S. S. Polar Heterobenzylic C(sp3)-H Chlorination Pathway Enabling Efficient Diversification of Aromatic Nitrogen Heterocycles. J. Am. Chem. Soc. 2023, 145, 36, 19832–19839.DOI: 10.1021/jacs.3c05822. Preprint.
274. Twilton, J.; Johnson, M. R.; Sidana, V.; Franke, M. C.; Bottecchia, C.; Lehnerr, D.; Lévesque, F.; Knapp, S. M. M.; Wang, L.; Gerken, J. B.; Hong, C. M.; Vickery, T. P.; Weisel, M. D.; Strotman, N. A.; Weix, D. J.; Root, T. W.; Stahl, S. S. Quinone-Mediated Hydrogen Anode to Support Scalable Ni-Catalyzed Cross-Electrophile Coupling. Nature, 2023, 623, 71-76.DOI:10.1038/s41586-023-06534-2. Preprint.
273. Stamoulis, A. G.; Bruns, D. L.; Stahl, S. S. Optimizing the Synthetic Potential of O2: Implications of Overpotential in Homogeneous Aerobic Oxidation Catalysis. J. Am. Chem. Soc. 2023, 145, 17515-17526. DOI: 10.1021/jacs.3c02887. Preprint.
272. Chen, S.-J.; He, C. Q.; Lin, S.; Krska, S. W.; Stahl, S. S. Accessing Three-Dimensional Molecular Diversity through Benzylic C–H Cross-Coupling. Nature Synth. 2023, 2, 998-1008. DOI: 10.1038/s44160-023-00332-4. Preprint.
271. Bates, J. S.; Johnson, M. R.; Khamespanah, F.; Root, T. W.; Stahl, S. S. Heterogeneous M-N-C Catalysts for Aerobic Oxidation Reactions: Lessons from Oxygen Reduction Electrocatalysts. Chem. Rev. 2023, 123, 6233–6256. DOI: 10.1021/acs.chemrev.2c00424. Preprint.
270. Golden, D. L.; Zhang, C.; Chen, S.-J.; Vasilopoulos, A.; Guzei, I. A.; Stahl, S. S. Benzylic C-H Esterification with Limiting C-H Substrate Enabled by Photochemical Redox Buffering of the Cu Catalyst. J. Am. Chem. Soc. 2023, 145, 9434–9440. DOI: 10.1021/jacs.3c01662. Preprint.
269. Carroll, G. M.; Gebbie, M. A.; Stahl, S. S.; Johnson, M. R.; Luca, O. R.; Petersen, H. A.; Bomble, Y. J.; Neale, N. R.; Cortight, R. D. Alternative Energy Carriers: Unique Interfaces for Electrochemical Hydrogenic Transformations. Adv. Energy Mater. 2023, 2203751. DOI: 10.1002/aenm.202203751. Preprint.
268. Su, Z.-M.; Twilton, J.; Hoyt, C. B.; Wang, F.; Stanley, L.; Mayes, H. B.; Kang, K.; Weix, D. J.; Beckham, G. T.; Stahl, S. S. Ni- and Ni/Pd-Catalyzed Reductive Coupling of Lignin-Derived Aromatics to Access Biobased Plasticizers. ACS Cent. Sci. 2023, 9, 159-165. DOI: 10.1021/acscentsci.2c01324. Preprint.
2022
267. Michael, K. H.; Su, Z.-M.; Wang, R.; Sheng, H.; Li, W.; Wang, F.; Stahl, S. S.; Jin, S. Pairing of Aqueous and Nonaqueous Electrosynthetic Reactions Enabled by a Redox Reservoir Electrode. J. Am. Chem. Soc. 2022, 144, 22641–22650. DOI: 10.1021/jacs.2c09632. Preprint.
266. Sullivan, K. P.; Werner, A. Z.; Ramirez, K. J.; Ellis, L. D.; Bussard, J. R.; Black, B. A.; Brandner, D. G.; Bratti, F.; Buss, B. L.; Dong, X.; Haugen, S. J.; Ingraham, M. A.; Konev, M. O.; Michener, W. E.; Miscall, J.; Pardo, I.; Woodworth, S. P.; Guss, A. M.; Román-Leshkov, Y.; Stahl, S. S.; Beckham, G. T. Mixed Plastics Waste Valorization Through Tandem Chemical Oxidation and Biological Funneling. Science 2022, 378 (6166), 207-211. DOI: 10.1126/science.abo4626. Preprint.
265. Bates, J. S.; Khamespanah, F.; Cullen, D. A.; Al-Omari, A. A.; Hopkins, M. N.; Martinez, J. J.; Root, T. W.; Stahl, S. S. Molecular Catalyst Synthesis Strategies to Prepare Atomically Dispersed Fe-N-C Heterogeneous Catalysts. J. Am. Chem. Soc. 2022, 144, 18797-18802. DOI: 10.1021/jacs.2c08884. Preprint.
264. Franke, M. C.; Longley, V. R.; Rafiee, M.; Stahl, S. S.; Hansen, E. C.; Weix, D. J. Zinc-free, Scalable Reductive Cross-Electrophile Coupling Driven by Electrochemistry in an Undivided Cell. ACS Catal. 2022, 12, 12617-12626. DOI: 10.1021/2c03033. Preprint.
263. Speelman, A. L.; Gerken, J. B.; Heins, S. P.; Wiedner, E. S.; Stahl, S. S.; Appel, A. M. Determining Overpotentials for the Oxidation of Alcohols by Molecular Electrocatalysts in Non-Aqueous Solvents. Energy Environ. Sci. 2022, 15, 4015-4024. DOI: 10.1039/D2EE01458K. Preprint.
262. Hoque, M. A.; Twilton, J.; Zhu, J.; Graaf, M. D.; Harper, K. C.; Tuca, E.; DiLabio, G. A.; Stahl, S. S. Electrochemical PINOylation of Methylarenes: Improving the Scope and Utility of Benzylic Oxidation through Mediated Electrolysis. J. Am. Chem. Soc. 2022, 144, 15295-15302. DOI: 10.1021/jacs.2c05974. Preprint.
261. Goes, S. L.; Nutting, J. E.; Hill, N. J.; Stahl, S. S.; Rafiee, M. Exploring Electrosynthesis: Bulk Electrolysis and Cyclic Voltammetry Analysis of the Shono Oxidation. J. Chem. Educ. 2022, 99, 3242-3248. DOI: 10.1021/acs.jchemed.2c00221. Preprint.
260. Westlie, A. H.; Chen, E. Y.-X.; Holland, C. M.; Stahl, S. S.; Doyle, M.; Trenor, S. R.; Knauer, K. M. Polyolefin Innovations toward Circularity and Sustainable Alternatives. Macromol. Rapid Commun. 2022, 2200492. DOI: 10.1002/marc.202200492.
259. Howland, W. C.; Gerken, J. B.; Stahl, S. S.; Surendranath, Y. Thermal Hydroquinone Oxidation on Co/N-doped Carbon Proceeds by a Band-Mediated Electrochemical Mechanism. J. Am. Chem. Soc. 2022, 144, 11253–11262. DOI: 10.1021/jacs.2c02746. Preprint.
258. Golden, D. L.; Suh, S.-E.; Stahl, S. S. Radical C(sp3)–H Functionalization and Cross-Coupling Reactions. Nat. Rev. Chem. 2022, 6, 405-427. DOI: 10.1038/s41570-022-00388-4. Preprint.
257. Bruns, D. L.; Stahl, S. S. Thermodynamic-Kinetic Comparison of Palladium(II)-Mediated Alcohol and Hydroquinone Oxidation. Organometallics 2022, 41, 3161-3166. DOI: 10.1021/acs.organomet.2c00017. Preprint.
256. Bates, J. S.; Biswas, S.; Suh, S.-E.; Johnson, M. R.; Mondal, B.; Root, T. W.; Stahl, S. S. Chemical and Electrochemical O2 Reduction on Earth-Abundant M-N-C Catalysts and Implications for Mediated Electrolysis. J. Am. Chem. Soc. 2022, 144, 922-927. DOI: 10.1021/jacs.1c11126. Preprint.
255. Lopez, M. A.; Buss, J. A.; Stahl, S. S. Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C-H Coupling with Oxidatively Sensitive Nucleophiles. Org. Lett. 2021, 24, 597-601. DOI: 10.1021/acs.orglett.1c04038. Preprint.
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2021
254. Alherech, M.; Omolabake, S.; Holland, C. M.; Klinger, G. E.; Hegg, E. L.; Stahl, S. S. From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography. ACS Cent. Sci. 2021, 7, 1831-1837. DOI: 10.1021/acscentsci.1c00729. Preprint.
253. Nutting, J. E.; Gerken, J. B.; Stamoulis, A. G.; Bruns, D. L.; Stahl, S. S. “How Should I Think about Voltage? What is Overpotential?”: Establishing an Organic Chemistry Intuition for Electrochemistry. J. Org. Chem. 2021, 86, 15875-15885. DOI: 10.1021/acs.joc.1c01520. Preprint.
252. Luo, H.; Weeda, E. P.; Alherech, M.; Anson, C. W.; Karlen, S. D.; Cui, Y.; Foster, C. E.; Stahl, S. S. Oxidative Catalytic Fractionation of Lignocellulosic Biomass under Non-alkaline Conditions. J. Am. Chem. Soc. 2021, 143, 15462-15470. DOI: 10.1021/jacs.1c08635. Preprint.
251. Chen, S.-J.; Golden, D. L.; Krska, S. W.; Stahl, S. S. Copper-Catalyzed Cross-Coupling of Benzylic C–H Bonds and Azoles with Controlled N-Site Selectivity. J. Am. Chem. Soc. 2021, 143, 14438-14444. DOI: 10.1021/jacs.1c07117. Preprint.
250. Stamoulis, A. G.; Geng, P.; Schmidt, M. A.; Eastgate, M. D.; Borovika, A.; Fraunhoffer, K. J.; Stahl, S. S. Sustainable Pd(OAc)2 Hydroquinone Cocatalyst System for Cis-Selective Dibenzoyloxylation of 1,3-Cyclohexadiene. Angew. Chem. Int. Ed. 2021, 60, 23182-23186. DOI: 10.1002/anie.202108499. Preprint.
249. Suh, S.-E.; Nkulu, L. E.; Lin, S.; Krska, S. W.; Stahl, S. S. Benzylic C–H Isocyanation/Amine Coupling Sequence Enabling High-Throughput Synthesis of Pharmaceutically Relevant Ureas. Chem. Sci. 2021, 12, 10380-10387. DOI: 10.1039/D1SC02049H. Preprint.
248. Nutting, J. E.; Mao, K.; Stahl, S. S. Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity. J. Am. Chem. Soc. 2021, 143, 10565-10570. DOI: 10.1021/jacs.1c05224. Preprint.
247. Kozack, C. V.; Tereniak, S. J.; Jaworski, J. N.; Li, B.; Bruns, D. L.; Knapp, S. M. M.; Landis, C. R.; Stahl, S. S. Benzoquinone Cocatalyst Contributions to DAF/Pd(OAc)2-Catalyzed Aerobic Allylic Acetoxylation in the Absence and Presence of a Co(salophen) Cocatalyst. ACS Catal. 2021, 11, 6363-6370. DOI: 10.1021/acscatal.1c01074. Preprint.
246. Jonathan, A.; Eagan, N. M.; Bruns, D. L.; Stahl, S. S.; Lanci, M. P.; Dumesic, J. A.; Huber, G. W. Ethylene Oligomerization into Linear Olefins Over Cobalt Oxide on Carbon Catalyst. Catal. Sci. Technol. 2021, 11, 3599-3608. DOI: 10.1039/d1cy00207d. Preprint.
245. Vasilopoulos, A.; Krska, S. W.; Stahl, S. S. C(sp3)–H Methylation Enabled by Peroxide Photosensitization and Ni-Mediated Radical Coupling. Science 2021, 372, 398-403. DOI: 10.1126/science.abh2623. Preprint.
244. Zhong, X.; Hoque, M. A.; Graaf, M. D.; Harper, K. C.; Wang, F.; Genders, J. D.; Stahl, S. S. Scalable Flow Electrochemical Alcohol Oxidation: Maintaining High Stereochemical Fidelity in the Synthesis of Levetiracetam. Org. Process Res. Dev. 2021, 25, 2601-2607. DOI: 10.1021/acs.oprd.1c00036. Preprint.
243. Salazar, C. A.; Thompson, B. J.; Knapp, S. M. M.; Myers, S. R.; Stahl, S. S. Multichannel Gas-Uptake/Evolution Reactor for Monitoring Liquid-Phase Chemical Reactions. Rev. Sci. Instrum. 2021, 92, 044103. DOI: 10.1063/5.0043007. Preprint.
242. Cui, Y.; Goes, S. L.; Stahl, S. S. Sequential Oxidation-Depolymerization Strategies for Lignin Conversion to Low Molecular Weight Aromatic Chemicals. Adv. Inorg. Chem. 2021, 77, 99-136. DOI: 10.1016/bs.adioch.2021.02.003. Preprint.
241. Wang, D.; Salazar, C. A.; Stahl, S. S. Catalyst-Controlled Regioselectivity in Pd-Catalyzed Aerobic Oxidative Arylation of Indoles. Organometallics 2021, 40, 2198-2203. DOI: 10.1021/acs.organomet.1c00139. Preprint.
240. Wang, F.; Sheng, H.; Li, W.; Gerken, J. B.; Jin, S.; Stahl, S. S. Stable Tetrasubtituted Quinone Redox Reservoir for Enhancing Decoupled Hydrogen and Oxygen Evolution. ACS Energy Lett. 2021, 6, 1533-1539. DOI: 10.1021/acsenergylett.1c00236. Preprint.
239. Liu, W.; Twilton, J.; Wei, B.; Lee, M.; Hopkins, M. N.; Bacsa, J.; Stahl, S. S.; Davies, H. M. L. Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant. ACS Catal. 2021, 11, 2676-2683. DOI: 10.1021/acscatal.1c00264. Preprint.
238. Yuan, Z.; Klinger, G. E.; Nikafshar, S.; Cui, Y.; Fang, Z.; Alherech, M.; Goes, S.; Anson, C.; Singh, S. K.; Bals, B.; Hodge, D. B.; Nejad, M.; Stahl, S. S.; Hegg, E. L. Effective Biomass Fractionation through Oxygen-Enhanced Alkaline–Oxidative Pretreatment. ACS Sustainable Chem. Eng. 2021, 9, 1118-1127. DOI: 10.1021/acssuschemeng.0c06170. Preprint.
237. Wang, F.; Li, W.; Wang, R.; Guo, T.; Sheng, H.; Fu, H.-C.; Stahl, S. S.; Jin, S. Modular Electrochemical Synthesis Using a Redox Reservoir Paired with Independent Half- Reactions. Joule 2021, 5, 149-165. DOI: 10.1016/j.joule.2020.11.011. Preprint.
236. Goes, S. L.; Mayer, M. N.; Nutting, J. E.; Hoober-Burkhardt, L. E.; Stahl, S. S.; Rafiee, M. Deriving the Turnover Frequency of Aminoxyl-Catalyzed Alcohol Oxidation by Chronoamperometry: An Introduction to Organic Electrocatalysis. J. Chem. Educ. 2021, 98, 600-606. DOI: 10.1021/acs.jchemed.0c01244. Preprint.
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2020
235. Salazar, C. A.; Flesch, K. N.; Haines, B. E.; Zhou, P. S.; Musaev, D. G.; Stahl, S. S. Tailored Quinones Support High-Turnover Pd Catalysts for Oxidative C–H Arylation with O2. Science 2020, 370, 1454–1460. DOI: 10.1126/science.abd1085. Preprint.
234. Bruns, D. L.; Musaev, D. G.; Stahl, S. S. Can Donor Ligands Make Pd(OAc)2 a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria. J. Am. Chem. Soc. 2020, 142, 19678–19688. DOI: 10.1021/jacs.0c09464. Preprint.
233. Tereniak, S. J.; Bruns, D. L.; Stahl, S. S. Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst. J. Am. Chem. Soc. 2020, 142, 20318–20323. DOI: 10.1021/jacs.0c09962. Preprint.
232. Wang, Y.-H.; Mondal, B.; Stahl, S. S. Molecular Cobalt Catalysts for O2 Reduction to H2O2: Benchmarking Performance via Rate–Overpotential Correlations. ACS Catal. 2020, 10, 12031-12039. DOI: 10.1021/acscatal.0c02197. Preprint.
231. Klinger, G. E.; Zhou, Y.; Foote, J. A.; Wester, A. M.; Cui, Y.; Alherech, M.; Stahl, S. S.; Jackson, J. E.; Hegg, E. L. Nucleophilic Thiols Reductively Cleave Ether Linkages in Lignin Model Polymers and Lignin. ChemSusChem 2020, 13, 4394–4399. DOI: 10.1002/cssc.202001238
230. Vasilopoulos, A.; Golden, D. L.; Buss, J. A.; Stahl, S. S. Copper-Catalyzed C–H Fluorination/Functionalization Sequence Enabling Benzylic C–H Cross Coupling with Diverse Nucleophiles. Org. Lett. 2020, 22, 5753-5757. DOI: 10.1021/acs.orglett.0c02238. Preprint.
229. Buss, J. A.; Vasilopoulos, A.; Golden, D. L.; Stahl, S. S. Copper-Catalyzed Functionalization of Benzylic C–H Bonds with N-Fluorobenzenesulfonimide: Switch from C–N to C–F Bond Formation Promoted by a Redox Buffer and Brønsted Base. Org. Lett. 2020, 22, 5749-5752. DOI: 10.1021/acs.orglett.0c02239. Preprint.
228. Suh, S.-E.; Chen, S.-J.; Mandal, M.; Guzei, I. A.; Cramer, C. J.; Stahl, S. S. Site-Selective Copper-Catalyzed Azidation of Benzylic C–H Bonds. J. Am. Chem. Soc. 2020, 142, 11388–11393. DOI: 10.1021/jacs.0c05362. Preprint.
227. Wang, F.; Gerken, J. B.; Bates, D. M.; Kim, Y. J.; Stahl, S. S. Electrochemical Strategy for Hydrazine Synthesis: Development and Overpotential Analysis of Methods for Oxidative N–N Coupling of an Ammonia Surrogate. J. Am. Chem. Soc. 2020, 142, 12349–12356. DOI: 10.1021/jacs.0c04626. Preprint.
226. Gerken, J. B.; Anson, C. W.; Preger, Y.; Symons, P. G.; Genders, J. D.; Qiu, Y.; Li, W.; Root, T. W.; Stahl, S. S. Comparison of Quinone‐Based Catholytes for Aqueous Redox Flow Batteries and Demonstration of Long‐Term Stability with Tetrasubstituted Quinones. Adv. Energy Mater. 2020, 10, 2000340. doi: 10.1002/aenm.202000340. Preprint.
225. Li, Y.; Karlen, S. D.; Demir, B.; Kim, H.; Luterbacher, J.; Dumesic, J. A.; Stahl, S. S.; Ralpha, J. Mechanistic Study of Diaryl Ether Bond Cleavage During Palladium-Catalyzed Lignin Hydrogenolysis. ChemSusChem 2020, 13, 4487 – 4494. doi: 10.1002/cssc.202000753. Preprint.
224. Preger, Y.; Johnson, M. R.; Biswas, S.; Anson, C. W.; Root, T. W.; Stahl, S. S. Anthraquinone-Mediated Fuel Cell Anode with an Off-Electrode Heterogeneous Catalyst Accessing High Power Density when Paired with a Mediated Cathode. ACS Energy Lett. 2020, 5, 1407-1412. doi: 10.1021/acsenergylett.0c00631. Preprint.
223. Anson, C. W.; Stahl, S. S. Mediated Fuel Cells: Soluble Redox Mediators and Their Applications to Electrochemical Reduction of O2 and Oxidation of H2, Alcohols, Biomass, and Complex Fuels. Chem. Rev. 2020, 120, 3749-3786. doi: 10.1021/acs.chemrev.9b00717. Preprint.
222. Salazar, C. A.; Gair, J. J.; Flesch, K. N.; Guzei, I. A.; Lewis, J. C.; Stahl, S. S. Catalytic Behavior of Mono-N-Protected Amino Acid Ligands in Ligand-Accelerated C-H Activation by Palladium(II). Angew. Chem. Int. Ed. 2020, 59, 10873-10877. doi: 10.1002/anie.202002484. Preprint.
221. Konnick, M. M.; Knapp, S. M. M.; Stahl, S. S. Mechanism of the Reaction of an NHC-Coordinated Palladium(II)-Hydride with O2 in Acetonitrile. Polyhedron 2020, 182, 114501-114508. doi: 10.1016/j.poly.2020.114501
Special issue in honor of Prof. John Bercaw on his 75th birthday.
220. Hu, H.; Chen, S.-J.; Mandal, M.; Praik, S. M.; Buss, J. A.; Krska, S. W.; Cramer, C. J.; Stahl, S. S. Copper-Catalyzed Benzylic C-H Coupling with Alcohols via Radical Relay Enabled by Redox Buffering. Nat. Catal. 2020, 3, 358-367. doi: 10.1038/s41929-020-0425-1. Preprint.
219. Wang, F.; Stahl, S. S. Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron-Proton Transfer Mediators. Acc. Chem. Res. 2020, 53, 561-574. DOI: 10.1021/acs.accounts.9b00544. Preprint.
218. Gerken, J. B.; Stamoulis, A. G.; Suh, S.-E.; Fischer, N. D.; Kim, Y.-J.; Guzei, I. A.; Stahl, S. S. Efficient Electrochemical Synthesis of Robust, Densely Functionalized Water Soluble Quinones. Chem. Commun. 2020, 56, 1199-1202. DOI: 10.1039/C9CC08878D. Preprint.
217. Ryan, M. C.; Kim, Y.-J.; Gerken, J. B.; Wang, F.; Aristov, M. M.; Martinelli, J. R.; Stahl, S. S. Mechanistic Insights into Copper-Catalyzed Aerobic Oxidative Coupling of N–N Bonds. Chem. Sci. 2020, 11, 1170-1175. DOI: 10.1039/C9SC04305E. Preprint.
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2019
216. Anson, C. W.; Stahl, S. S. Processes for Electrochemical Production of Electrolyte-Free Hydrogen Peroxide. Joule 2019, 3, 2889-2891. DOI: 10.1016/j.joule.2019.11.017
215. Rafiee, M.; Alherech, M.; Karlen, S. D.; Stahl, S. S. Electrochemical Aminoxyl-Mediated Oxidation of Primary Alcohols in Lignin to Carboxylic Acids: Polymer Modification and Depolymerization. J. Am. Chem. Soc. 2019, 141, 15266-15276. DOI: 10.1021/jacs.9b07243. Preprint.
214. Ryan, M. C.; Whitmire, L. D.; McCann, S. D.; Stahl, S. S. Copper/TEMPO Redox Redux: Analysis of PCET Oxidation of TEMPOH by Copper(II) and the Reaction of TEMPO with Copper(I). Inorg. Chem. 2019, 58, 10194-10200. DOI: 10.1021/acs.inorgchem.9b01326. Preprint.
213. Das, A.; Nutting, J. E.; Stahl, S. S. Electrochemical C–H Oxygenation and Alcohol Dehydrogenation Involving Fe-oxo Species Using Water as the Oxygen Source. Chem. Sci. 2019, 10, 7542-7548. DOI: 10.1039/C9SC02609F
212. Piszel, P. E.; Vasilopoulos, A.; Stahl, S. S. Oxidative Amide Coupling from Functionally Diverse Alcohols and Amines using Aerobic Copper/Nitroxyl Catalysis. Angew. Chem. Int. Ed. 2019, 131, 12211-12215. DOI: 10.1002/anie.201906130. Preprint.
211. Jaworski, J. N.; Kozack, C. V.; Tereniak, S. J.; Knapp, S. M. M.; Landis, C. R.; Miller, J. T.; Stahl, S. S. Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C–H Acetoxylation Catalyzed by Pd(OAc)2/4,5-Diazafluoren-9-one. J. Am. Chem. Soc. 2019, 141, 10462-10474. DOI:10.1021/jacs.9b04699. Preprint.
210. Sing, S. K.; Savoy, A.; Yuan, Z.; Luo, H.; Stahl, S. S.; Hegg, E. L.; Hodge, D. B. Integrated Two-Stage Alkaline-Oxidative Pretreatment of Hybrid Poplar. Part 1: Impact of Alkaline Pre-Extraction Conditions on Process Performance and Lignin Properties. Ind. Eng. Chem. Res. 2019, 58, 15989-15999. DOI:10.1021/acs.iecr.9b01124
209. Wang, Y.-H.; Schneider, P. E.; Goldsmith, Z. K.; Mondal, B.; Hammes-Schiffer, S.; Stahl, S. S. Brønsted Acid Scaling Relationships Enable Control Over Product Selectivity from O2 Reduction with a Mononuclear Cobalt Porphyrin Catalyst. ACS Cent. Sci. 2019, 5, 1024-1034. DOI:10.1021/acscentsci.9b00194
208. Kozack, C. V.; Sowin, J. A.; Jaworski, J. N.; Iosub, A. V.; Stahl, S. S. Aerobic Acyloxylation of Allylic C–H Bonds Initiated by a Pd0 Precatalyst with 4,5‐Diazafluoren‐9‐one as an Ancillary Ligand. ChemSusChem 2019, 12, 3003-3007. DOI:10.1002/cssc.201900727. Preprint.
207. Perez, J. M.; Kontur, W. S.; Alherech, M.; Coplien, J.; Karlen, S. D.; Stahl, S. S.; Donohue, T. J.; Noguera, D. R. Funneling aromatic products of chemically depolymerized lignin into 2-pyrone-4-6-dicarboxylic acid with Novosphingobium aromaticivorans. Green Chem. 2019, 21, 1340-1350. DOI: 10.1039/C8GC03504K
206. Wang, F.; Stahl, S. S. Merging Photochemistry with Electrochemistry: Functional Group Tolerant Electrochemical Amination of sp³ C–H Bonds. Angew. Chem. Int. Ed. 2019, 58, 6385-6390. DOI:10.1002/anie.201813960. Preprint.
205. Li, B.; Wendlandt, A. E.; Stahl, S. S. Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates. Org. Lett. 2019, 21, 1176-1181. DOI:10.1021/acs.orglett.9b00111. Preprint.
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2018
204. Preger, Y.; Gerken, J. B.; Biswas, S.; Anson, C. W.; Johnson, M. R.; Root, T. W.; Stahl, S. S. Quinone-Mediated Electrochemical O2 Reduction Accessing High Power Density with an Off-Electrode Co-N/C Catalyst. Joule 2018, 2, 2722-2731. DOI: 10.1016/j.joule.2018.09.010
203. Lennox, A. J. J.; Goes, S. L.; Webster, M. P.; Koolman, H. F.; Djuric, S. W.; Stahl, S. S. Electrochemical Aminoxyl-Mediated α-Cyanation of Secondary Piperidines for Pharmaceutical Building Block Diversification. J. Am. Chem. Soc. 2018, 140, 11227-11231. DOI:10.1021/jacs.8b08145. Preprint.
202. Wang, Y.-H.; Goldsmith, Z. K.; Schneider, P. E.; Anson, C. W.; Gerken, J. B.; Ghosh, S.; Hammes-Schiffer, S.; Stahl, S. S. Kinetic and Mechanistic Characterization of Low-Overpotential, H2O2-Selective Reduction of O2 Catalyzed by N2O2-Ligated Cobalt Complexes. J. Am. Chem. Soc. 2018, 140, 10890-10899. DOI:10.1021/jacs.8b06394
201. Ryan, M. C.; Martinelli, J. R.; Stahl, S. S. Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling. J. Am. Chem. Soc. 2018, 140, 9074-9077. DOI:10.1021/jacs.8b05245. Preprint.
200. Rafiee, M.; Konz, Z. M.; Graaf, M. D.; Koolman, H. F.; Stahl, S. S. Electrochemical Oxidation of Alcohols and Aldehydes to Carboxylic Acids by 4-Acetamido-TEMPO: An Alternative to “Anelli” and “Pinnick” Oxidations. ACS Catal. 2018, 8, 6738-6744. DOI:10.1021/acscatal.8b01640
199. Preger, Y.; Root, T. W.; Stahl, S. S. Platinum-Based Heterogenous Catalysts for Nitrile Synthesis via Aerobic Oxidative Coupling of Alcohols and Ammonia. ACS Omega 2018, 3, 6091-6096. DOI:10.1021/acsomega.8b00911
198. Wang, F.; Rafiee, M.; Stahl, S. S. Electrochemical Functional-Group-Tolerant Shono-Type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators. Angew. Chem. Int. Ed. 2018, 57, 6686-6690. DOI:10.1002/anie.201803539
197. Nutting, J. E.; Rafiee, M.; Stahl, S. S. Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions. Chem. Rev. 2018, 118, 4834-4885. DOI:10.1021/acs.chemrev.7b00763. Preprint.
196. Wang, D.; Weinstein, A. B.; White, P. B.; Stahl, S. S. Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions. Chem. Rev. 2018, 118, 2636-2679. DOI:10.1021/acs.chemrev.7b00334
195. Tereniak, S. J.; Landis, C. R.; Stahl, S. S. Are Phosphines Viable Ligands for Pd-Catalyzed Aerobic Oxidation Reactions? Contrasting Insights from a Survey of Six Reactions. ACS Catal. 2018, 8, 3708-3714. DOI:10.1021/acscatal.8b01009
194. Das, A.; Rahimi, A.; Ulbrich, A.; Alherech, M.; Motagamwala, A. H.; Bhalla, A.; da Costa Sousa, L.; Balan, V.; Dumesic, J. A.; Hegg, E. L.; Dale, B. E.; Ralph, J.; Coon, J. J.; Stahl, S. S. Lignin Conversion to Low-Molecular-Weight Aromatics via an Aerobic Oxidation-Hydrolysis Sequence: Comparison of Different Lignin Sources. ACS Sustainable Chem. Eng. 2018, 6, 3367-3374. DOI:10.1021/acssuschemeng.7b03541
193. Mannel, D. S.; King, J.; Preger, Y.; Ahmed, M. S.; Root, T. W.; Stahl, S. S. Mechanistic Insights into Aerobic Oxidative Methyl Esterification of Primary Alcohols with Heterogeneous PdBiTe Catalysts. ACS Catal. 2018, 8, 1038-1047. DOI:10.1021/acscatal.7b02886
192. Rafiee, M.; Wang, F.; Hruszkewycz, D. P.; Stahl, S. S. N-Hydroxyphthalimide-Mediated Electrochemical Iodination of Methylarenes and Comparison to Electron-Transfer-Initiated C–H Functionalization. J. Am. Chem. Soc. 2018, 140, 22-25. DOI:10.1021/jacs.7b09744. Preprint.
191. Gerken, J. B.; Pang, Y. Q.; Lauber, M. B.; Stahl, S. S. Structural Effects on the pH-Dependent Redox Properties of Organic Nitroxyls: Pourbaix Diagrams for TEMPO, ABNO, and Three TEMPO Analogs. J. Org. Chem. 2018, 83, 7323-7330. DOI:10.1021/acs.joc.7b02547
190. Lennox, A. J. J.; Nutting, J. E.; Stahl, S. S. Selective Electrochemical Generation of Benzylic Radicals Enabled by Ferrocene-Based Electron-Transfer Mediators. Chem. Sci. 2018, 9, 356-361. DOI:10.1039/C7SC04032F
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2017
189. Anson, C. W.; Stahl, S. S. Cooperative Electrocatalytic O2 Reduction Involving Co(salophen) with p-Hydroquinone as an Electron–Proton Transfer Mediator. J. Am. Chem. Soc. 2017, 139, 18472-18475. DOI:10.1021/jacs.7b11362
188. Wang, Y.-H.; Pegis, M. L.; Mayer, J. M.; Stahl, S. S. Molecular Cobalt Catalysts for O2 Reduction: Low-Overpotential Production of H2O2 and Comparison with Iron-Based Catalysts. J. Am. Chem. Soc. 2017, 139, 16458-16461. DOI:10.1021/jacs.7b09089
187. Tereniak, S. J.; Stahl, S. S. Mechanistic Basis for Efficient, Site-Selective, Aerobic Catalytic Turnover in Pd-Catalyzed C–H Imidoylation of Heterocycle-Containing Molecules. J. Am. Chem. Soc. 2017, 139, 14533-14541. DOI:10.1021/jacs.7b07359
186. Walroth, R. C.; Miles, K. C.; Lukens, J. T.; MacMillan, S. M.; Stahl, S. S.; Lancaster, K. M. Electronic Structural Analysis of Copper(II)–TEMPO/ABNO Complexes Provides Evidence for Copper(I)–Oxoammonium Character. J. Am. Chem. Soc. 2017, 139, 13507-13517. DOI:10.1021/jacs.7b07186
185. Ahmed, M. S.; Mannel, D. S.; Root, T. W.; Stahl, S. S. Aerobic Oxidation of Diverse Primary Alcohols to Carboxylic Acids with a Heterogeneous Pd-Bi-Te/C (PBT/C) Catalyst. Org. Process Res. Dev. 2017, 21, 1388-1393. DOI:10.1021/acs.oprd.7b00223
184. Das, A.; Stahl, S. S. Non-Covalent Immobilization of Molecular Electrocatalysts for Chemical Synthesis: Efficient Electrochemical Alcohol Oxidation with a Pyrene-TEMPO Conjugate. Angew. Chem. Int. Ed. 2017, 56, 8892-8897. DOI:10.1002/anie.201704921. Preprint.
183. Vasilopoulos, A.; Zultanski, S. L.; Stahl, S. S. Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes. J. Am. Chem. Soc. 2017, 139, 7705-7708. DOI:10.1021/jacs.7b03387
182. Wang, D.; Stahl, S. S. Pd-Catalyzed Aerobic Oxidative Biaryl Coupling: Non-Redox Cocatalysis by Cu(OTf)2 and Discovery of Fe(OTf)3 as a Highly Effective Cocatalyst. J. Am. Chem. Soc. 2017, 139, 5704-5707. DOI:10.1021/jacs.7b01970. Preprint.
181. Goldsmith, Z. K.; Harshan, A. K.; Gerken, J. B.; Vörös, M.; Galli, G.; Stahl, S. S.; Hammes-Schiffer, S. Characterization of NiFe oxyhydroxide electrocatalysts by integrated electronic structure calculations and spectroelectrochemistry. Proc. Natl. Acad. Sci. U.S.A. 2017, 114, 3050-3055. DOI:10.1073/pnas.1702081114
180. McCann, S. D.; Lumb, J.-P.; Arndtsen, B. A.; Stahl, S. S. Second-Order Biomimicry: In Situ Oxidative Self-Processing Converts Copper(I)/Diamine Precursor into a Highly Active Aerobic Oxidation Catalyst. ACS Cent. Sci. 2017, 3, 314-321. DOI:10.1021/acscentsci.7b00022
179. Jaworski, J. N.; McCann, S. D.; Guzei, I. A.; Stahl, S. S. Detection of Palladium(I) in Aerobic Oxidation Catalysis. Angew. Chem., Int. Ed. 2017, 56, 3605-3610. DOI:10.1002/anie.201700345. Preprint.
178. Mannel, D. S.; Ahmed, M. S.; Root, T. W.; Stahl, S. S. Discovery of Multicomponent Heterogeneous Catalysts via Admixture Screening: PdBiTe Catalysts for Aerobic Oxidative Esterification of Primary Alcohols. J. Am. Chem. Soc. 2017, 139, 1690-1698. DOI:10.1021/jacs.6b12722
177. Hruszkewycz, D. P.; Miles, K. C.; Thiel, O. R.; Stahl, S. S. Co/NHPI-mediated aerobic oxygenation of benzylic C–H Bonds in pharmaceutically relevant molecules. Chem. Sci. 2017, 8, 1282-1287. DOI:10.1039/C6SC03831J
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2016
176. Huynh, M. T.; Anson, C. W.; Cavell, A. C.; Stahl, S. S.; Hammes-Schiffer, S. Quinone 1 e– and 2 e–/2 H+ Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships. J. Am. Chem. Soc. 2016, 138, 15903–15910. DOI:10.1021/jacs.6b05797. Preprint.
175. Iosub, A. V.; Stahl, S. S. Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products. ACS. Catal. 2016, 6, 8201-8213. DOI:10.1021/acscatal.6b02406. Preprint.
174. Zhang, W.; Wang, F.; McCann, S. D.; Wang, D.; Chen, P.; Stahl, S. S.; Liu, G. Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay. Science 2016, 353, 1014-1018. DOI:10.1126/science.aaf7783
173. Miles, K. C.; Abrams, L. M.; Landis, C. R.; Stahl, S. S. KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation. Org. Lett. 2016, 18, 3590–3593. DOI:10.1021/acs.orglett.6b01598. Preprint.
172. Clagg, K.; Hou, H.; Weinstein, A. B.; Russell, D.; Stahl, S. S.; Koenig, S. G. Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C–H Bonds. Org. Lett. 2016, 18, 3586–3589. DOI:10.1021/acs.orglett.6b01592. Preprint.
171. Badalyan, A.; Stahl, S. S. Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators. Nature 2016, 535, 406–410. DOI:10.1038/nature18008
170. Zultanski, S. L.; Zhao, J.; Stahl, S. S. Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines. J. Am. Chem. Soc. 2016, 138, 6416–6419. DOI:10.1021/jacs.6b03931. Preprint.
169. White, P. B.; Jaworski, J. N.; Geyunjian, H. Z.; Stahl, S. S. Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions. ACS Catal. 2016, 6, 3340-3348. DOI:10.1021/acscatal.6b00953. Preprint.
168. White, P. B.; Jaworski, J. N.; Fry, C. G.; Dolinar, B. S.; Guzei, I. A.; Stahl, S. S. Structurally Diverse Diazafluorene-Ligated Palladium(II) Complexes and Their Implications for Aerobic Oxidation Reactions. J. Am. Chem. Soc. 2016, 138, 4869-4880. DOI:10.1021/jacs.6b01188. Preprint.
167. Anson, C. W.; Ghosh, S.; Hammes-Schiffer, H.; Stahl, S. S. Co(salophen)-Catalyzed Aerobic Oxidation of p-Hydroquinone: Mechanism and Implications for Aerobic Oxidation Catalysis. J. Am. Chem. Soc. 2016, 138, 4186-4193. DOI:10.1021/jacs.6b00254
166. Shaner, S. E.; Hooker, P. D.; Nickel, A.-M.; Leichtfuss, A. R.; Adams, C. S.; de la Cerda, D.; She, Y.; Gerken, J. B.; Pokhrel, R.; Ambrose, N. J.; Khaliqi, D.; Stahl, S. S.; Schuttlefield Christus, J. D. Discovering Inexpensive, Effective Catalysts for Solar Energy Conversion: An Authentic Research Laboratory Experience. J. Chem. Ed. 2016, 93, 650-657. DOI:10.1021/acs.jchemed.5b00591
165. McCann, S. D.; Stahl, S. S. Mechanism of Copper/Azodicarboxylate-Catalyzed Aerobic Alcohol Oxidation: Evidence for Uncooperative Catalysis. J. Am. Chem. Soc. 2016, 138, 199-206. DOI:10.1021/jacs.5b09940
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2015
164. Chen, J. Y. C.; Dang, L.; Liang, H.; Bi, W.; Gerken, J. B.; Jin, S.; Alp, E. E.; Stahl, S. S. Operando Analysis of NiFe and Fe Oxyhydroxide Electrocatalysts for Water Oxidation: Detection of Fe4+ by Mössbauer Spectroscopy. J. Am. Chem. Soc. 2015, 137, 15090-15093. DOI:10.1021/jacs.5b10699a
163. Rafiee, M; Miles, K. C.; Stahl, S. S. Electrocatalytic Alcohol Oxidation with TEMPO and Bicyclic Nitroxyl Derivatives: Driving Force Trumps Steric Effects. J. Am. Chem. Soc. 2015, 137, 14751–14757. DOI:10.1021/jacs.5b09672. Preprint.
162. Wendlandt, A. E.; Stahl, S. S. Quinone-Catalyzed Selective Oxidation of Organic Molecules. Angew. Chem. Int. Ed. 2015, 54, 14638-14658. DOI:10.1002/anie.201505017. Preprint.
161. Steves, J. E.; Stahl, S. S. Stable TEMPO and ABNO Catalyst Solutions for User-Friendly (bpy)Cu/Nitroxyl-Catalyzed Aerobic Alcohol Oxidation. J. Org. Chem. 2015, 80, 11184–11188. DOI:10.1021/acs.joc.5b01950
160. Iosub, A. V.; Stahl, S. S. Catalytic Aerobic Dehydrogenation of Nitrogen Heterocycles Using Heterogeneous Cobalt Oxide Supported on Nitrogen-Doped Carbon. Org. Lett. 2015, 17, 4404-4407. DOI:10.1021/acs.orglett.5b01790. Preprint.
159. Gerken, J. B.; Stahl, S. S. High-Potential Electrocatalytic O2 Reduction with Nitroxyl/NOx Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis. ACS Cent. Sci. 2015, 1, 234-243. DOI:10.1021/acscentsci.5b00163
158. Steves, J. E.; Preger, Y.; Martinelli, J. R.; Welch, C. J.; Root, T. W.; Hawkins, J. M.; Stahl, S. S. Process Development of CuI/ABNO/NMI-Catalyzed Aerobic Alcohol Oxidation. Org. Process Res. Dev. 2015, 19, 1548–1553. DOI:10.1021/acs.oprd.5b00179
157. Zheng, C.; Stahl, S. S. Regioselective Aerobic Oxidative Heck Reactions with Electronically Unbiased Alkenes: Efficient Access to α-Alkyl Vinylarene. Chem. Commun. 2015, 51, 12771–12774. DOI:10.1039/C5CC05312A. Preprint.
156. Pokhrel, R.; Goetz, M. K.; Shaner, S. E.; Wu X.; Stahl, S. S. The “Best Catalyst” for Water Oxidation Depends on the Oxidation Method Employed: A Case Study of Manganese Oxides. J. Am. Chem. Soc. 2015, 137, 8384–8387. DOI:10.1021/jacs.5b05093
155. Greene, J. F.; Preger, Y.; Stahl, S. S.; Root, T. W. PTFE-Membrane Flow Reactor for Aerobic Oxidation Reactions and Its Application to Alcohol Oxidation. Org. Process Res. Dev. 2015, 19, 858–864. DOI:10.1021/acs.oprd.5b00125
154. McCann, S. D.; Stahl, S. S. Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst. Acc. Chem. Res. 2015, 48, 1756–1766. DOI:10.1021/acs.accounts.5b00060
153. Zultanski, S. L.; Stahl, S. S. Palladium-catalyzed aerobic acetoxylation of benzene using NOx-based redox mediators. J. Organomet. Chem. 2015, 793, 263-268. DOI:10.1016/j.jorganchem.2015.03.003. Preprint.
152. Miles, K. C.; Stahl, S. S. Practical Aerobic Alcohol Oxidation with Cu/Nitroxyl and Nitroxyl/NOx Catalyst Systems. Aldrichimica Acta 2015, 48, 8-10.
151. Xie, X.; Stahl, S. S. Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols. J. Am. Chem. Soc. 2015, 137, 3767–3770. DOI:10.1021/jacs.5b01036
150. Iosub, A. V.; Stahl, S. S. Palladium-Catalyzed Aerobic Oxidative Dehydrogenation of Cyclohexenes to Substituted Arene Derivatives. J. Am. Chem. Soc. 2015, 137, 3454–3457. DOI:10.1021/ja512770u. Preprint.
149. Parajuli, R.; Gerken, J. B.; Keyshar, K.; Sullivan, I.; Sivasankar, N.; Teamey, K.; Stahl, S. S.; Cole E. B. Integration of Anodic and Cathodic Catalysts of Earth-Abundant Materials for Efficient, Scalable CO2 Reduction. Top. Catal. 2015, 58, 57-66. DOI:10.1007/s11244-014-0345-x
148. Kim, J.; Stahl, S. S. Cu-Catalyzed Aerobic Oxidative Three-Component Coupling Route to N-Sulfonyl Amidines via an Ynamine Intermediate. J. Org. Chem. 2015, 80, 2448–2454. DOI:10.1021/jo5029198
147. Osterberg, P. M.; Niemeier, J. K.; Welch, C. J.; Hawkins, J. M.; Martinelli, J. R.; Johnson, T. E.; Root, T. W; Stahl, S. S. Experimental Limiting Oxygen Concentrations for Nine Organic Solvents at Temperatures and Pressures Relevant to Aerobic Oxidations in the Pharmaceutical Industry. Org. Process Res. Dev. 2015, 19, 1537–1543. DOI:10.1021/op500328f. Preprint.
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2014
146. Rahimi, A.; Ulbrich, A.; Coon, J. J.; Stahl S. S. Formic-acid-induced depolymerization of oxidized lignin to aromatics. Nature 2014, 515, 249–252. DOI:10.1038/nature13867
145. Mannel, D. S.; Stahl, S. S; Root, T. W. Continuous Flow Aerobic Oxidation Reactions Using a Heterogeneous Ru(OH)x/Al2O3 Catalyst. Org. Process Res. Dev. 2014, 18, 1503–1508. DOI:10.1021/op5002676
144. Stephenson, N. A.; Gellman, S. H.; Stahl, S. S. Ammonolysis of anilides promoted by ethylene glycol and phosphoric acid. RSC Adv. 2014, 4, 46840-46843. DOI:10.1039/C4RA09065A
143. Wendlandt, A. E.; Stahl, S. S. Modular o‑Quinone Catalyst System for Dehydrogenation of Tetrahydroquinolines under Ambient Conditions. J. Am. Chem. Soc. 2014, 136, 11910–11913. DOI:10.1021/ja506546w. Preprint.
142. Ryland, B. L.; McCann, S. D.; Brunold, T. C.; Stahl, S. S. Mechanism of Alcohol Oxidation Mediated by Copper(II) and Nitroxyl Radicals. J. Am. Chem. Soc. 2014, 136, 12166–12173. DOI:10.1021/ja5070137
141. Weinstein, A. B.; Stahl, S. S. Palladium catalyzed aryl C–H amination with O2 via in situ formation of peroxide-based oxidant(s) from dioxane. Catal. Sci. Technol. 2014, 4, 4301-4307. DOI:10.1039/C4CY00764F. Preprint.
140. Ryland, B. L.; Stahl, S. S. Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems. Angew. Chem. Int. Ed. 2014, 53, 8824-8838. DOI:10.1002/anie.201403110. Preprint.
139. Diao,T.; Stahl, S. S. O2-promoted allylic acetoxylation of alkenes: Assessment of “push” versus “pull” mechanisms and comparison between O2 and benzoquinone. Polyhedron 2014, 84, 96–102. DOI:10.1016/j.poly.2014.06.038. Preprint.
138. White, P. B. and Stahl, S. S. 4,5-Diazafluoren-9-one. e-EROS 2014, , 1-3. DOI:10.1002/047084289X.rn01700
137. Wang, D.; Izawa, Y.; Stahl, S. S. Pd-Catalyzed Aerobic Oxidative Coupling of Arenes: Evidence for Transmetalation between Two Pd(II)-Aryl Intermediates. J. Am. Chem. Soc. 2014, 136, 9914-9917. DOI:10.1021/ja505405u
136. Gerken, J. B.; Shaner, S. E.; Massé, R. C.; Porubsky, N. J.; Stahl, S. S. A survey of diverse earth abundant oxygen evolution electrocatalysts showing enhanced activity from Ni-Fe oxides containing a third metal. Energy Environ. Sci. 2014, 7, 2376-2382. DOI:10.1039/C4EE00436A
135. Gladysz, J. A.; Bedford, R. B.; Fujita, M.; Gabbaı̈, F. P.; Goldberg, K. I.; Holland, P. L.; Kiplinger, J. L.; Krische, M. J.; Louie, J.; Lu, C. C.; Norton, J. R.; Petrukhina, M. A.; Ren, T.; Stahl, S. S.; Tilley, T. D.; Webster, C. E.; White, M. C.; Whiteker, G. T. Organometallics Roundtable 2013–2014. Organometallics 2014, 33, 1505-1527. DOI:10.1021/om500253z
134. Stahl, S. S.; Diao, T. Oxidation Adjacent to C=X bonds by Dehydrogenation. Comp. Org. Synth. 2014, 7, 178-212. DOI:10.1016/B978-0-08-097742-3.00707-2
133. Chen, J. Y. C.; Miller, J. T.; Gerken, J. B.; Stahl, S. S. Inverse Spinel NiFeAlO4 as a Highly Active Oxygen Evolution Electrocatalyst: Promotion of Activity by a Redox-Inert Metal Ion. Energy Environ. Sci. 2014, 7, 1382-1386. DOI:10.1039/C3EE43811B
132. Tsybizova, A.; Ryland, B. L.; Tsierkezos, N.; Stahl, S. S.; Roithová, J.; Schröder, D. Speciation Behavior of Copper(II) Acetate in Simple Organic Solvents – Revealing the Effect of Trace Water. Eur. J. Inorg. Chem. 2014, 1407-1412. DOI:10.1002/ejic.201400036
131. Wendlandt, A. E.; Stahl, S. S. Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst. J. Am. Chem. Soc. 2014, 136, 506-512. DOI:10.1021/ja411692v
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2013
130. Hoover, J. M.; Ryland, B. L; Stahl, S. S. Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems. ACS Catal. 2013, 3, 2599–2605. DOI:10.1021/cs400689a. Preprint.
129. Lauber, M. B.; Stahl, S. S. Efficient Aerobic Oxidation of Secondary Alcohols at Ambient Temperature with an ABNO/NOx Catalyst System. ACS Catal. 2013, 3, 2612–2616. DOI:10.1021/cs400746m
128. Steves, J. E.; Stahl, S. S. Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems. J. Am. Chem. Soc. 2013, 135, 15742-15745. DOI:10.1021/ja409241h. Preprint.
127. Weinstein, A. B.; Schuman, D. P.; Tan, Z. X.; Stahl, S. S. Synthesis of Vicinal Aminoalcohols by Stereoselective Aza-Wacker Cyclizations: Access to (−)-Acosamine by Redox Relay. Angew. Chem. Int. Ed. 2013, 51, 11867-11870. DOI:10.1002/anie.20130592. Preprint.
126. Greene, J. F.; Hoover, J. M.; Mannel, D. S.; Root, T. W.; Stahl, S. S. Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst. Org. Process Res. Dev. 2013, 17, 1247-1251. DOI:10.1021/op400207f
125. Powell, A. B.; Stahl, S. S. Aerobic Oxidation of Diverse Primary Alcohols to Methyl Esters with a Readily Accessible Heterogeneous Pd/Bi/Te Catalyst. Org. Lett. 2013, 15, 5072-5075. DOI:10.1021/ol402428e
124. Hong, W. P.; Iosub, A. V.; Stahl, S. S. Pd-Catalyzed Semmler–Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines. J. Am. Chem. Soc. 2013, 135, 13664–13667. DOI:10.1021/ja4073172. Preprint.
123. Kim, J.; Stahl, S.S. Cu/Nitroxyl-Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature. ACS Catal. 2013, 3, 1652-1656. DOI:10.1021/cs400360e. Preprint.
122. Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. Divergence between Organometallic and Single-Electron Transfer Mechanisms in Copper(II)-Mediated Aerobic C–H Oxidation. J. Am. Chem. Soc. 2013, 135, 9797–9804. DOI:10.1021/ja4026424
121. Martinez, C.; Wu, Y.; Weinstein, A. B.; Stahl, S. S.; Liu, G.; Muniz, K. Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)2 on Aminopalladation Stereoselectivity. J. Org. Chem. 2013, 78, 6309–6315. DOI:10.1021/jo400671q. Preprint.
120. Pun, D.; Diao, T.; Stahl, S. S. Aerobic Dehydrogenation of Cyclohexanone to Phenol Catalyzed by Pd(TFA)2/2-Dimethylaminopyridine: Evidence for the Role of Pd-Nanoparticles. J. Am. Chem. Soc. 2013, 135, 8213–8221. DOI:10.1021/ja403165u. Preprint.
119. Diao, T.; Pun, D.; Stahl, S. S. Aerobic Dehydrogenation of Cyclohexanone to Cyclohexenone Catalyzed by Pd(DMSO)2(TFA)2: Evidence for Ligand-Controlled Chemoselectivity. J. Am. Chem. Soc. 2013, 135, 8205–8212. DOI:10.1021/ja4031648. Preprint.
118. Hoover, J. M.; Stahl, S. S. Air Oxidation of Primary Alcohols Catalyzed by Copper(I)/TEMPO. Preparation of 2-Amino-5-bromo-benzaldehyde. Org. Synth. 2013, 90, 240-250. 13OS Hoover PDF
117. Rahimi, A.; Azarpira, A.; Kim, H.; Ralph, J.; Stahl, S. S. Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin. J. Am. Chem. Soc. 2013, 135, 6415–6418. DOI:10.1021/ja401793n
116. Gerken, J. B.; Rigsby, M. L.; Ruther, R. E.; Perez-Rodriguez, R. J.; Guzei, I. A., Hamers, R. J.; Stahl, S. S. Modular Synthesis of Alkyne-Substituted Ruthenium Polypyridyl Complexes Suitable for “Click” Coupling. Inorg. Chem.2013, 52, 2796–2798. DOI:10.1021/ic302827s
115. Izawa, Y.; Zheng, C.; Stahl, S. S. Aerobic Oxidative Heck/Dehydrogenation Reactions of Cyclohexenones: Efficient Access to meta-Substituted Phenols. Angew. Chem. Int. Ed. 2013, 52, 3672-3675. DOI:10.1002/anie.201209457. Preprint.
114. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation. J. Am. Chem. Soc. 2013, 135, 2357-2367. DOI:10.1021/ja3117203. Preprint.
113. Ye, X.; White, P. B.; Stahl, S. S. Mechanistic Studies of Wacker-Type Amidocyclization of Alkenes Catalyzed by (IMes)Pd(TFA)2(H2O): Kinetic and Stereochemical Implications of Proton Transfer. J. Org. Chem. 2013, 78, 2083-2090. DOI:10.1021/jo302266t. Preprint.
112. Hill, N. J.; Hoover, J. M.; Stahl, S. S. Aerobic Alcohol Oxidation Using a Copper(I)/TEMPO Catalyst System: A Green, Catalytic Oxidation Reaction for the Undergraduate Organic Chemistry Laboratory. J. Chem. Educ. 2013, 90, 102-105. DOI:10.1021/ed300368q
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2012
111. Diao, T.; White, P.; Guzei, I.; Stahl, S. S. Characterization of DMSO Coordination to Palladium(II) in Solution and Insights into the Aerobic Oxidation Catalyst, Pd(DMSO)2(TFA)2. Inorg. Chem. 2012, 51, 11898-11909. DOI:10.1021/ic301799p. Preprint.
110. Weinstein, A. B.; Stahl, S. S. Reconciling the Stereochemical Course of Nucleopalladiation with the Development of Enantioselective Wacker-Type Cyclizations. Angew. Chem. Int. Ed. 2012, 51, 11505-11509. DOI:10.1002/anie.201206702. Preprint.
109. Zheng, C.; Wang, D.; Stahl, S. S. Catalyst-Controlled Regioselectivity in the Synthesis of Branched Conjugated Dienes via Aerobic Oxidative Heck Reactions. J. Am. Chem. Soc. 2012, 134, 16496-16499. DOI:10.1021/ja307371w. Preprint.
108. King, A. E.; Ryland, B. L.; Brunold, T. C.; Stahl, S. S. Kinetic and Spectroscopic Studies of Aerobic Copper(II)-Catalyzed Methoxylation of Arylboronic Esters and Instights into Aryl Transmetalation to Copper(II). Organometallics 2012, 31, 7948–7957. DOI:10.1021/om300586p. Preprint.
107. Rigsby, M. L.; Mandal, S.; Nam, W.; Spencer, L. C.; Llobet, A.; Stahl, S. S. Cobalt analogs of Ru-based water oxidation catalysts: Overcoming thermodynamic instability and kinetic lability to achieve electrocatalytic O2 evolution. Chem. Sci. 2012, 3, 3058-3062. DOI:10.1039/C2SC20755A
106. Hoover, J. M.; Steves, J. E.; Stahl, S. S. Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air. Nat. Protoc. 2012, 7, 1161-1167. DOI:10.1038/nprot.2012.057. Preprint.
105. Gerken, J. B.; Chen, J. Y. C.; Massé, R. C.; Powell, A. B.; Stahl, S. S. Development of O2-Sensitive Fluorescence-Quenching Assay for the Combinatorial Discovery of Electrocatalysts for Water Oxidation. Angew. Chem. Int. Ed. 2012, 51, 6676-6680. DOI:10.1002/anie.201201999
104. Zhang, J.; Markiewicz, M. J.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Functionally Diverse Nylon-3 Copolymers from Readily Accessible β-Lactams. ACS Macro Lett. 2012, 1, 714-717. DOI:10.1021/mz300172y
103. Wendlandt, A. E.; Stahl, S. S. Chemoselective Organocatalytic Aerobic Oxidation of Primary Amines to Secondary Imines. Org. Lett. 2012, 14, 2850-2853. DOI:10.1021/ol301095j
102. Wendlandt, A. E.; Stahl, S. S. Copper(II)-mediated oxidative cyclization of enamides to oxazoles. Org. Biomol. Chem. 2012, 10, 3866-3870. DOI:10.1039/C2OB25310K
101. Lu, Z.; Stahl, S. S. Intramolecular Pd(II)-Catalyzed Aerobic Oxidative Amination of Alkenes: Synthesis of Six-Membered N-Heterocycles. Org. Lett. 2012, 14, 1234-1237. DOI:10.1021/ol300030w. Preprint.
100. Redford, J. E.; McDonald, R. I.; Rigsby, M. L.; Wiensch, J. D.; Stahl, S. S. Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Wacker-Type Aerobic Oxidative Cyclization of Alkenes with tert-Butanesulfinamide Nucleophiles. Org. Lett. 2012, 14, 1242-1245. DOI:10.1021/ol3000519. Preprint.
99. Campbell, A. N.; Stahl, S. S. Overcoming the “Oxidant Problem”: Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu). Acc. Chem. Res. 2012, 45, 851-863. DOI:10.1021/ar2002045. Preprint.
98. Zhang, Z.; Markiewicz, M. J.; Mowery, B. P.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. C-Terminal Functionalization of Nylon-3 Polymers: Effects of C-Terminal Groups on Antibacterial and Hemolytic Activities. Biomacromolecules 2012, 13, 323-331. DOI:10.1021/bm2013058
97. Diao, T.; Wadzinski, T. J.; Stahl, S. S. Direct Aerobic α,β-Dehydrogenation of Aldehydes and Ketones with a Pd(TFA)2/4,5-Diazafluorenone Catalyst. Chem. Sci. 2012, 3, 887-891. DOI:10.1039/C1SC00724F. Preprint.
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2011
96. White, P. B.; Stahl, S. S. Reversible Alkene Insertion into the Pd-N Bond of Pd(II)-Sulfonamidates and Implications for Catalytic Amidation Reactions. J. Am. Chem. Soc. 2011, 133, 18594-18597. DOI:10.1021/ja208560h. Preprint.
95. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Copper-Catalyzed Aerobic Oxidative C-H Functionalizations: Trends and Mechanistic Insights. Angew. Chem. Int. Ed. 2011, 50, 11062-11087. DOI:10.1002/anie.201103945
94. Hoover, J. M.; Stahl, S. S. Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols. J. Am. Chem. Soc. 2011, 133, 16901-16910. DOI:10.1021/ja206230h. Preprint.
93. Diao, T.; Stahl, S. S. Synthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones. J. Am. Chem. Soc. 2011, 133, 14566-14569. DOI:10.1021/ja206575j. Preprint.
92. Campbell, A. N.; Meyer, E. B.; Stahl, S. S. Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands. Chem. Commun. 2011, 47, 10257-10259. DOI:10.1039/C1CC13632A. Preprint.
91. Gerken, J. B.; McAlpin, J. G.; Chen, J. Y. C.; Rigsby, M. L.; Casey, W. H.; Britt, R. D.; Stahl, S. S. Electrochemical Water Oxidation with Cobalt-Based Electrocatalysts from pH 0-14: The Thermodynamic Basis for Catalyst Structure, Stability, and Activity. J. Am. Chem. Soc. 2011, 133, 14431-14442. DOI:10.1021/ja205647m
90. Huffman, L. M.; Casitas, A.; Font, M.; Canta, M.; Costas, M.; Ribas, X.; Stahl, S. S. Observation and Mechanistic Study of Facile C-O Bond Formation Between a Well-Defined Aryl-Copper(III) Complex and Oxygen Nucleophiles. Chem. Eur. J. 2011, 17, 10643-10650. DOI:10.1002/chem.201100608
89. Decharin, N.; Popp, B. V.; Stahl, S. S. Reaction of O2 with [(-)-Sparteine]Pd(H)Cl: Evidence for an Intramolecular [H-L]+ “Reductive Elimination” Pathway. J. Am. Chem. Soc. 2011, 133, 13268-13271. DOI:10.1021/ja204989p. Preprint.
88. Benson, M. C.; Ruther, R. E.; Gerken, J. B.; Rigsby, M. L.; Bishop, L. M.; Tan, Y.; Stahl, S. S.; Hamers, R. J. Modular “Click” Chemistry for Electrochemically and Photoelectrochemically Active Molecular Interfaces to Tin Oxide Surfaces. ACS Appl. Mater. Interfaces 2011, 3, 3110-3119. DOI:10.1021/am200615r
87. Izawa, Y.; Pun, D.; Stahl, S. S. Palladium-Catalyzed Aerobic Dehydrogenation of Substituted Cyclohexanones to Phenols. Science 2011, 333, 209-213. DOI:10.1126/science.1204183. Preprint.
86. Huffman, L. M.; Stahl, S. S. Mechanistic analysis of trans C-N reductive elimination from a square-planar macrocyclic aryl-copper(III) complex. Dalton Trans. 2011, 40, 8959-8963. DOI:10.1039/C1DT10463B
85. McDonald, R. I.; White, P. B.; Weinstein, A. B.; Tam, C. P.; Stahl, S. S. Enantioselective Pd(II)-Catalyzed Aerobic Oxidative Amidation of Alkenes and Insights into the Role of Electronic Asymmetry in Pyridine-Oxazoline Ligands. Org. Lett. 2011, 13, 2830-2833. DOI:10.1021/ol200784y. Preprint.
84. Decharin, N.; Stahl, S. S. Benzoquinone-Promoted Reaction of O2 with a PdII Hydride. J. Am. Chem. Soc. 2011, 133, 5732-5735. DOI:10.1021/ja200957n
83. Ruther, R. E.; Rigsby, M. L.; Gerken, J. B.; Hogendoorn, S. R.; Landis, E. C.; Stahl, S. S.; Hamers, R. J. Highly Stable Redox-Active Molecular Layers by Covalent Grafting to Conductive Diamond. J. Am. Chem. Soc.2011, 133, 5692-5694. DOI:10.1021/ja200210t
82. McDonald, R. I.; Liu, G.; Stahl, S. S. Palladium(II)-Catalyzed Alkene Functionalization via Nucleopalladation: Stereochemical Pathways and Enantioselective Catalytic Applications. Chem. Rev. 2011, 111, 2981-3019. DOI:10.1021/cr100371y. Preprint.
81. Ye, X.; Liu, G.; Popp, B. V.; Stahl, S. S. Mechanistic Studies of Wacker-Type Intramolecular Aerobic Oxidative Amination of Alkenes Catalyzed by Pd(OAc)2/Pyridine. J. Org. Chem. 2011, 76, 1031-1044. DOI:10.1021/jo102338a. Preprint.
80. Konnick, M. M.; Decharin, N.; Popp, B. V.; Stahl, S. S. O2 insertion into a palladium(II)-hydride bond: Observation of mechanistic crossover between HX-reductive-elimination and hydrogen-atom-abstraction pathways. Chem. Sci. 2011, 2, 326-330. DOI:10.1039/C0SC00392A
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2010
79. Izawa, Y.; Stahl, S. S. Aerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed C-H Functionalization. Adv. Synth. Catal. 2010, 352, 3223-3229. DOI:10.1002/adsc.201000771. Preprint.
78. Campbell, A. N.; White, P. B.; Guzei, I. A.; Stahl, S. S. Allylic C-H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy to Achieve Aerobic Catalytic Turnover. J. Am. Chem. Soc. 2010, 132, 15116-15119. DOI:10.1021/ja105829t. Preprint.
77. Casitas, A.; Poater, A.; Sola, M.; Stahl, S. S.; Costas, M.; Ribas, X. Molecular mechansim of acid-triggered aryl-halide reductive elimination in well-defined aryl-CuIII-halide species. Dalton Trans. 2010, 39, 10458-10463. DOI:10.1039/C0DT00284D
76. McDonald, R. I.; Wong, G. W.; Neupane, R. P.; Stahl, S. S.; Landis, C. R. Enantioselective Hydroformylation of N-Vinyl Carboxamides, Allyl Carbamates, and Allyl Ethers Using Chiral Diazaphospholane Ligands. J. Am. Chem. Soc. 2010, 132, 14027-14029. DOI:10.1021/ja106674n. Preprint.
75. Gerken, J. B.; Landis, E. C.; Hamers, R. J.; Stahl, S. S. Fluoride-Modulated Cobalt Catalysts for Electrochemical Oxidation of Water under Non-Alkaline Conditions. ChemSusChem 2010, 3, 1176-1179. DOI:10.1002/cssc.201000161
74. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. Copper-Catalyzed Aerobic Oxidative Functionalization of an Arene C-H Bond: Evidence for an Aryl-Copper(III) Intermediate. J. Am. Chem. Soc. 2010, 132, 12068-12073. DOI:10.1021/ja1045378
73. Popp, B. V.; Morales, C. M.; Landis, C. R.; Stahl, S. S. Electronic Structural Comparison of the Reactions of Dioxygen and Alkenes with Nitrogen-Chelated Palladium(0). Inorg. Chem. 2010, 49, 8200-8207. DOI:10.1021/ic100806w
72. McDonald, R. I.; Stahl, S. S. Modular Synthesis of 1,2-Diamine Derivatives by Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides. Angew. Chem. Int. Ed. 2010, 49, 5529-5532. DOI:10.1002/anie.200906342. Preprint.
71. Ye, X.; Johnson, M. D.; Diao, T.; Yates, M. H.; Stahl, S. S. Development of safe and scalable continuous-flow methods for palladium-catalyzed aerobic oxidation reactions. Green Chem. 2010, 12, 1180-1186. DOI:10.1039/C0GC00106F. Preprint.
70. Casitas, A.; King, A. E.; Parella, T.; Costas, M.; Stahl, S. S.; Ribas, X. Direct observation of CuI/CuIII redox steps relevant to Ullmann-type coupling reactions. Chem. Sci. 2010, 1, 326-330. DOI:10.1039/C0SC00245C
69. Zhang, J.; Gellman, S. H.; Stahl, S. S. Kinetics of Anionic Ring-Opening Polymerization of Variously Substituted β-Lactams: Homopolymerization and Copolymerization. Macromolecules 2010, 43, 5618-5626. DOI:10.1021/ma1010809
68. Dohm, M. T.; Mowery, B. P.; Czyzewski, A. M.; Stahl, S. S.; Gellman, S. H.; Barron, A. E. Biophysical Mimicry of Lung Surfactant Protein B by Random Nylon-3 Copolymers. J. Am. Chem. Soc. 2010, 132, 7957-7967. DOI:10.1021/ja909734n
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2009
67. Lee, M.-R.; Stahl, S. S.; Gellman, S. H.; Masters, K. S. Nylon-3 Copolymers that Generate Cell-Adhesive Surfaces Identified by Library Screening. J. Am. Chem. Soc. 2009, 131, 16779-16789. DOI:10.1021/ja9050636
66. Yang, L.; Lu, Z.; Stahl, S. S. Regioselective Copper-Catalyzed Chlorination and Bromination of Arenes with O2 as the Oxidant. Chem. Commun. 2009, 6460-6462. DOI:10.1039/B915487F
65. Stephenson, N. S.; Zhu, J.; Gellman, S. H.; Stahl, S. S. Catalytic Transamidation Reactions Compatible with Tertiary Amide Metathesis under Ambient Conditions. J. Am. Chem. Soc. 2009, 131, 10003-10008. DOI:10.1021/ja8094262
64. Mowery, B. P.; Lindner, A. H.; Weisblum, B.;Stahl, S. S.; Gellman, S. H. Structure-activity Relationships among Random Nylon-3 Copolymers that Mimic Antibacterial Host-Defense Peptides. J. Am. Chem. Soc. 2009, 131, 9735-9745. DOI:10.1021/ja901613g
63. Scarborough, C. C.; Bergant, A.;Sazamaa, G.T.; Guzeia, I.A.; Spencera, L.C.; Stahl, S. S. Synthesis of Pd(II) Complexes Bearing an Enantiomerically-Resolved Seven-Membered N-Heterocyclic Carbene Ligands and Initial Studies of their Use in Asymmetric Wacker-Type Oxidative Cyclization Reactions. Tetrahedron 2009, 65, 5084-5092. DOI:10.1016/j.tet.2009.04.072. Preprint.
62. King, A. E.; Brunold, T. C.; Stahl, S. S. Mechanistic Study of Copper-Catalyzed Aerobic Oxidative Coupling of Arylboronic Esters and Methanol: Insights into an Organometallic Oxidase Reaction. J. Am. Chem. Soc. 2009, 131, 5044-5045. DOI:10.1021/ja9006657
61. Scarborough, C. C.; McDonald, R I.; Hartmann, C.; Sazama, G. T.; Bergant, A.; Stahl, S. S. Steric Modulation of Chiral Biaryl Diamines via Pd-Catalyzed Directed C−H Arylation. J. Org. Chem. 2009, 74, 2613-2615. DOI:10.1021/jo802632v. Preprint.
60. Scarborough, C. C.; Guzei, I. A.; Stahl, S. S. Synthesis and Isolation of a Stable, Axially-Chiral Seven-Membered N-Heterocyclic Carbene. Dalton Trans. 2009, 2284-2286. DOI:10.1039/B902460C. Preprint.
59. Popp, B. V. ; Stahl, S. S. Mechanism of Pd(OAc)2/Pyridine Catalyst Reoxidation by O2: Influence of Labile Monodentate Ligands and Identification of a Biomimetic Mechanism for O2 Activation. Chem. Eur. J. 2009, 15, 2915-2922. DOI:10.1002/chem.200802311
58. Zhang, J.;Kissounko, D. A.; Lee, S. E.; Gellman, S. H.; Stahl, S. S. Access to Poly-β-Peptides with Functionalized Side Chains and End Groups via Controlled Ring-Opening Polymerization of β-Lactams. J. Am. Chem. Soc. 2009, 131, 1589-1597. DOI:10.1021/ja8069192
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2008
57. Lee, M.; Stahl, S. S.; Gellman, S. H. Synthesis of β-Lactams Bearing Functionalized Side Chains from a Readily Available Precursor. Org. Lett. 2008, 10, 5317-5319. DOI:10.1021/ol802274x
56. Epand, R. F.; Mowery, B. P.; Lee, S. E.; Stahl, S. S.; Lehrer, R. I.; Gellman, S. H.; Epand, R. M. Dual Mechanism of Bacterial Lethality for a Cationic Sequence-Random Copolymer that Mimics Host-Defense Antimicrobial Peptides. J. Mol. Biol. 2008, 279, 38-50. DOI:10.1016/j.jmb.2008.03.047
55. Hewgley, J. B.; Stahl, S. S.; Kozlowski, M. C. Mechanistic Study of Asymmetric Oxidative Biaryl Coupling: Evidence for Self-Processing of the Copper Catalyst to Achieve Control of Oxidase vs Oxygenase Activity. J. Am. Chem. Soc. 2008, 130, 12232-12233. DOI:10.1021/ja804570b
54. Huffman, L. M.; Stahl, S. S. Carbon-Nitrogen Bond Formation Involving Well-Defined Aryl-CopperIII Complexes. J. Am. Chem. Soc. 2008, 130, 9196-9197. DOI:10.1021/ja802123p
53. Konnick, M. M.; Stahl, S. S. Reaction of Molecular Oxygen with a PdII-Hydride To Produce a PdII-Hydroperoxide: Experimental Evidence for an HX-Reductive-Elimination Pathway. J. Am. Chem. Soc. 2008, 130, 5753-5762. DOI:10.1021/ja7112504
52. Hamada, T.; Ye, X.; Stahl, S. S. Copper-Catalyzed Aerobic Oxidative Amidation of Terminal Alkynes: Efficient Synthesis of Ynamides. J. Am. Chem. Soc. 2008, 130, 833-835. DOI:10.1021/ja077406x
51. Hoerter, J. M.; Otte, K. M.; Gellman, S. H.; Cui, Q.; Stahl, S. S. Discovery and Mechanistic Study of AlIII-Catalyzed Transamidation of Tertiary Amides. J. Am. Chem. Soc. 2008, 130, 647-654. DOI:10.1021/ja0762994
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2007
50. Mowery, B. P.; Lee, S. E.; Kissounko, D. A.; Epand, R. F.; Epand, R. M.; Weisblum, B.; Stahl, S. S.; Gellman, S. H. Mimicry of Antimicrobial Host-Defense Peptides by Random Copolymers. J. Am. Chem. Soc. 2007, 129, 15474-15476. DOI:10.1021/ja077288d
49. Rogers, M. M.; Kotov, V.; Chatwichien, J.; Stahl, S. S. Palladium-Catalyzed Oxidative Amination of Alkenes: Improved Catalyst Reoxidation Enables the Use of Alkene as the Limiting Reagent. Org. Lett. 2007, 9, 4331-4334. DOI:10.1021/ol701903r
48. Liu, G.; Stahl, S. S. The Two-Faced Reactivity of Alkenes: Cis – Versus Trans- Aminopalladation in Aerobic Pd- Catalyzed Intramolecular Aza-Wacker Reactions. J. Am. Chem. Soc. 2007, 129, 6328-6335. DOI:10.1021/ja070424u
47. Popp, B. V.; Stahl, S. S. Insertion of Molecular Oxygen into a Pd-Hydride Bond: Computational Evidence for Two Nearly Isoenergetic Pathways. J. Am. Chem. Soc. 2007, 129, 4410-4422. DOI:10.1021/ja069037v
46. Kotov, V.; Scarborough , C. C.; Stahl, S. S. Palladium-Catalyzed Aerobic Oxidative Amination of Alkenes: Development of Intra- and Intermolecular Aza-Wacker Reactions. Inorg. Chem. 2007, 46, 1910-1923. DOI:10.1021/ic061997v
45. Popp, B. V.; Wendlandt, J. E.; Landis, C. R.; Stahl, S. S. Reaction of Molecular Oxygen with an NHC-Coordinated Pd0 Complex: Computational Insights and Experimental Implications. Angew. Chem. Int. Ed. 2007, 46, 601-604. DOI:10.1002/anie.200603667
44. Bell, C. Kissounko, D. A.; Gellman, S. H.; Stahl, S. S. Catalytic Metathesis of Simple Secondary Amides. Angew. Chem. Int. Ed. 2007, 46, 761-763. DOI:10.1002/anie.200603588
43. Kissounko, D. A.; Hoerter, J. M.; Guzei, I. A.; Cui, Q.; Gellman, S. H.; Stahl, S. S. TiIV – Mediated Reactions between Primary Amines and Secondary Carboxamides: Amidine Formation Versus Transamidation. J. Am. Chem. Soc. 2007, 129, 1776-1783. DOI:10.1021/ja0650293
42. Popp, B. V.; Stahl, S. S. Palladium-Catalyzed Oxidation Reactions: Comparison of Benzoquinone and Molecular Oxygen as Stoichiometric Oxidants. In Organometallic Oxidation Catalysis, Meyer, F., Limberg, C. Eds.; Springer: New York, Topics in Organometallic Chemistry 2007, 22, 149-189. DOI:10.1007/3418_039
41. Rogers, M. M.; Stahl, S. S. N-Heterocyclic Carbenes as Ligands for High-Oxidation-State Metal Complexes and Oxidation Catalysis. In N-Heterocyclic Carbenes in Transition Metal Catalysis, Glorius, F., Ed.; Springer: New York, Topics in Organometallic Chemistry 2007, 21, 21-46. DOI:10.1007/978-3-540-36930-1_2
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2006
40. Scarborough , C. C.; Stahl, S. S. Synthesis of Pyrrolidines via Palladium(II)-Catalyzed Aerobic Oxidative Carboamination of Butyl Vinyl Ether and Styrenes with Allyl Tosylamides. Org. Lett. 2006, 8, 3251-3254. DOI:10.1021/ol061057e
39. Liu, G.; Stahl, S. S. Highly Regioselective Pd-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and Evidence for cis -Aminopalladation and SN2 C-O Bond Formation. J. Am. Chem. Soc. 2006, 128, 7179-7181. DOI:10.1021/ja061706h
38. Rogers, M. M.; Wendlandt, J. E.; Guzei, I. A.; Stahl, S. S. Aerobic Intramolecular Oxidative Amination of Alkenes Catalyzed by NHC-Coordinated Palladium Complexes. Org. Lett. 2006, 8, 2257-2260. DOI:10.1021/ol060327q
37. Konnick, M. M.; Gandhi, B. A.; Guzei, I. A.; Stahl, S. S. Reaction of Molecular Oxygen with a PdII-Hydride to Produce a PdII-Hydroperoxide: Acid Catalysis and Implications for Pd-Catalyzed Aerobic Oxidation Reactions. Angew. Chem. Int. Ed. 2006, 45, 2904-2907. DOI:10.1002/anie.200600532
36. Hoerter, J. M.; Otte, K. M.; Gellman, S. H.; Stahl, S. S. Mechanism of AluminumIII-Catalyzed Transamidation of Unactivated Secondary Carboxamides. J. Am. Chem. Soc. 2006, 128, 5177. DOI:10.1021/ja060331x
35. Steinhoff, B. A.; Stahl, S. S. Mechanism of Pd(OAc)2/DMSO-Catalyzed Aerobic Alcohol Oxidation: Mass-Transfer-Limitation Effects and Catalyst Decomposition Pathways. J. Am. Chem. Soc. 2006, 128, 4348-4355. DOI:10.1021/ja057914b
34. Popp, B. V.; Stahl, S. S. ‘Oxidatively-Induced’ Reductive Elimination of Dioxygen from an η2-Peroxopalladium(II) Complex Promoted by Electron-Deficient Alkenes. J. Am. Chem. Soc. 2006, 128, 2804-2805. DOI:10.1021/ja057753b
33. Steinhoff, B. A.; King, A. E.; Stahl, S. S. Unexpected Roles of Molecular Sieves in Palladium-Catalyzed Aerobic Oxidation Reactions. J. Org. Chem. 2006, 71, 1861-1868. DOI:10.1021/jo052192s
32. Popp, B. V.; Thorman, J. L.; Stahl, S. S. Similarities Between the Reactions of Dioxygen and Alkenes with Palladium(0): Relevance to the Use of Benzoquinone and Molecular Oxygen as Stoichiometric Oxidants in Palladium-Catalyzed Oxidation Reactions. J. Mol. Catal., A: Chem. 2006, 251, 2-7. DOI:10.1016/j.molcata.2006.02.019
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2005
31. Timokhin, V. I. ; Stahl, S. S. Brønsted Base-Modulated Regioselectivity in the Aerobic Oxidative Amination of Styrene Catalyzed by Palladium. J. Am. Chem. Soc. 2005, 127, 17888-17893. DOI: 10.1021/ja0562806
30. Stahl, S. S. Palladium-Catalyzed Oxidation of Organic Chemicals with O2. Science 2005, 309, 1824-1826. DOI: 10.1126/science.1114666
29. Kissounko, D. A.; Guzei, I. A.; Gellman, S. H.; Stahl, S. S. Titanium(IV)-Mediated Conversion of Carboxamides to Amidines and Implications for Catalytic Transamidation. Organometallics 2005, 24, 5208-5210. DOI: 10.1021/om050768y
28. Scarborough, C. C.; Popp, B. V.; Guzei, I. A.; Stahl, S. S. Development of 7-Membered N-Heterocyclic Carbene Ligands for Transition Metals. J. Organomet. Chem. 2005, 690, 6143-6155. DOI: 10.1016/j.jorganchem.2005.08.022
27. Scarborough, C. C.; Grady, M. J. W.; Guzei, I. A.; Gandhi, B. A.; Bunel, E. E.; Stahl, S. S. PalladiumII Complexes Possessing a Seven-Membered N-Heterocyclic Carbene Ligand. Angew. Chem. Int. Ed. 2005, 44, 5269-5272. DOI:10.1002/anie.200501522
26. Eldred, S. E.; Pancost, M. R.; Otte, K. M.; Rozema, D.; Stahl, S. S.; Gellman, S. H. Effects of Side Chain Configuration and Backbone Spacing on the Gene Delivery Properties of Lysine-Derived Cationic Polymers. Bioconjugate Chem. 2005, 16, 694-699. DOI:10.1021/bc050017c
25. Brice, J. L.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. Aerobic Oxidative Amination of Unactivated Alkenes Catalyzed by Palladium. J. Am. Chem. Soc. 2005, 127, 2868-2869. DOI:10.1021/ja0433020
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2004
24. Landis, C. R.; Morales, C. M.; Stahl, S. S. Insights into the Spin-Forbidden Reaction between L2Pd0 and Molecular Oxygen. J. Am. Chem. Soc. 2004, 126, 16302-16303. DOI:10.1021/ja044674b
23. Popp, B. V.; Thorman, J. L.; Morales, C. M.; Landis, C. R.; Stahl, S. S. “Inverse-Electron-Demand” Ligand Substitution: Experimental and Computational Insights into Olefin Exchange at Palladium(0). J. Am. Chem. Soc. 2004, 126, 14832-14842. DOI:10.1021/ja0459734
22. Steinhoff, B. A.; Guzei, I. A.; Stahl S. S. Mechanistic Characterization of Aerobic Alcohol Oxidation Catalyzed by Pd(OAc)2 / Pyridine Including Identification of the Catalyst Resting State and the Origin of Non-Linear [Catalyst] Dependence. J. Am. Chem. Soc. 2004, 126, 11268-11278. DOI:10.1021/ja049962m
21. Konnick, M. M.; Guzei, I. A.; and Stahl, S. S. Characterization of Peroxo and Hydroperoxo Intermediates in the Aerobic Oxidation of N-Heterocyclic-Carbene-Coordinated Palladium(0). J. Am. Chem. Soc. 2004, 126, 10212-10213. DOI:10.1021/ja046884u
20. Stahl, S. S. Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals via Direct Dioxygen-Coupled Catalytic Turnover. Angew. Chem. Int. Ed. 2004, 43, 3400-3420. DOI:10.1002/anie.200300630
19. Brice, J. l.; Meerdink, J. M.; Stahl, S. S. Formation of Enamides via Palladium(II)-Catalyzed Vinyl Transfer from Vinyl Ethers to Nitrogen Nucleophiles. Org. Lett. 2004, 6, 1845-1848. DOI:10.1021/ol0494360
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2003
18. Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. Dioxygen-Coupled Oxidative Amination of Styrene. J. Am. Chem. Soc. 2003, 125, 12996-12997. DOI:10.1021/ja0362149. Preprint.
17. Eldred, S. E.; Stone, D. A.; Gellman, S. H.; Stahl, S. S. Catalytic Transamidation under Moderate Conditions. J. Am. Chem. Soc. 2003, 125, 3422-3423. DOI:10.1021/ja028242h
16. Stahl, S. S.; Thorman, J. L.; de Silva, N.; Guzei, I. A.; Clark, R. W. ‘Inverse-Electron-Demand’ Ligand Substitution in Palladium(0) Olefin Complexes. J. Am. Chem. Soc. 2003, 125, 12-13. DOI:10.1021/ja028738z
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2002
15. Drier, T. O.; Stahl, S. S. The Wisconsin Schlenk Line: Incorporation of an Ergonomic Greaseless Three-Way Valve Design. Fusion 2002, 3, 25-27.
14. Steinhoff, B. A.; Stahl, S. S. Ligand-Modulated Palladium Oxidation Catalysis: Mechanistic Insights into Aerobic Alcohol Oxidation with the Pd(OAc)2 / Pyridine Catalyst System. Org. Lett. 2002, 4, 4179-4181. DOI:10.1021/ol026988e
13. Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. Mechanistic Study of Alcohol Oxidation by the Pd(OAc)2/O2/DMSO Catalyst System and Implications for the Development of Improved Aerobic Oxidation Catalysts. J. Am. Chem. Soc. 2002, 124, 766-767. DOI:10.1021/ja016806w
12. Fix, S. R.; Brice, J. L.; Stahl, S. S. Efficient Intramolecular Oxidative Amination of Olefins through Direct Dioxygen-Coupled Palladium Catalysis. Angew. Chem. Int. Ed. 2002, 41, 164-166. DOI:10.1002/1521-3773(20020104)41:1<164::AID-ANIE164>3.0.CO;2-B
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2001
11. Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. Oxygenation of Nitrogen-Coordinated Palladium(0): Synthetic, Structural and Mechanistic Studies and Implications for Aerobic Oxidation Catalysis. J. Am. Chem. Soc. 2001, 123, 7188-7189. DOI:10.1021/ja015683c
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Before UW-Madison
10. Oxygen Kinetic Isotope Effects in Methane Monooxygenase.
9. Dioxygen and Alkane Activation by Iron-Containing Enzymes.
8. Mechanistic Studies of the Reaction of Reduced Methane Monooxygenase Hydroxylase with Dioxygen and Substrates.
7. Homogeneous Oxidation of Alkanes by Electrophilic Late Transition Metals.
6. Investigation of the Factors Affecting the Stability of Dihydrogen Adducts of Platinum(II).
5. Alkylplatinum(II) Intermediates in C-H Activation by Platinum Complexes in Aqueous Solution.
4. Exploring the Mechanism of Aqueous C-H Activation by Pt(II) through Model Chemistry: Evidence for the Intermediacy of Alkylhydridoplatinum(IV) and Alkane σ-Adducts.
3. Formation and Reductive Elimination of a Hydridoalkylplatinum(IV) Intermediate upon Protonolysis of an Alkylplatinum(II) Complex.
2. C-H Activation by Aqueous Platinum Complexes: A Mechanistic Model.
1. Oxidation of Zeise’s Salt by [PtCl6]2- : A Mechanistic Model for Hydrocarbon Oxidation.
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Patents
20. Stahl, S.; Tereniak, S. Method for Aerobic Oxidative Coupling of Thiophenes with a Ligand-Supported Palladium Catalyst. US Patent 10858334 B2, December 8, 2020.
19. Hegg, E. L.; Yuan, Z.; Hodge, D. B.; Stahl. S. S.; Bals, B. D. Economical Methods for Performing Oxidative Catalytic Pretreatment of Plant Biomass Using a Homogeneous Catalyst System. US Patent Application US 2020/0332376 A1, October 22, 2020.
18. Stahl, S. S.; Gerken, J. B.; Anson, C. W.; Root, T. W.; Preger, Y. Flow-Based Anode for the Electrocatalytic Oxidation of a Fuel or Other Reductant. US Patent 10727518 B2, July 28, 2020.
17. Stahl, S. S.; Gerken, J. B. High Solubility Thioether Quinones. US Patent 10597359 B2, March 24, 2020.
Continuation Patent: US Patent 11021441 B2, June 1, 2021.
16. Stahl, S. S.; Rafiee, M. Polycarboxylated Compounds and Compositions Containing Same. US Patent 10336868 B2, July 2, 2019.
Continuation Patent: US Patent 11028235 B2, June 8, 2021.
15. Stahl, S. S.; Biswas, S.; Anson, C. W.; Preger, Y.; Root, T. Flow-Based Cathode with Immobilized Non-Platinum Transition Metal Redox Catalyst. US Patent Application US 2019/0131650 A1, May 2, 2019.
14. Stahl, S. S.; Rafiee, M. Nitroxyl-Mediated Oxidation of Lignin and Polycarboxylated Products. US Patent 9903028 B2, February 27, 2018.
13. Stahl, S. S.; Gerken, J. B.; Anson, C. W. Charge Transfer Mediator Based Systems for Electrocatalytic Oxygen Reduction. US Patent 9711818 B2, July 18, 2017.
Continuation Patent: US Patent 9812727 B2, November 7, 2017.
12. Stahl, S.S.; Powell, A.B.; Root, T.W.; Mannel, D.S.; Ahmed, M.S. Conversion of Alcohols to Alkyl Esters and Carboxylic Acids Using Heterogeneous Palladium-Based Catalysts. US Patent 9593064 B2, March 14, 2017.
Divisional Patent: US Patent 9957217 B2, May 1, 2018.
11. Stahl, S. S.; Coon, J.; Rahimi, A.; Ulbrich, A. Selective C-O Bond Cleavage of Oxidized Lignin and Lignin-Type Materials into Simple Aromatic Compounds. US Patent 9359391 B2, June 7, 2016.
10. Gellman, S. H.; Stahl, S. S.; Mowery, B. P.; Barron, A.; Dohm, M. Nylon-3 Co-Polymers and Synthetic Lung Surfactant Compositions Containing Same. US Patent 9044392 B2, June 2, 2015.
Divisional Patent: US Patent 9925213 B2, March 27, 2018.
Continuation Patent: US Patent 10736915 B2, August 11, 2020.
9. Stahl, S. S.; Rahimi, A. Selective Aerobic Alcohol Oxidation Method for Conversion of Lignin into Simple Aromatic Compounds. US Patent 8969534 B2, March 3, 2015.
8. Gerken, J. B.; Stahl, S. S. Buffered Cobalt Oxide Catalysts. US Patent 8956525 B2, February 17, 2015.
Divisional Patent: US Patent 9534305 B2, January 3, 2017.
7. Stahl, S. S.; Gerken, J. B.; Chen, J. Y.; Massé, R. C.; Shaner, S. E.; Porubsky, N. J. Catalysts Having Mixed Metal Oxides. US Patent Application US 2013/0206608 A1, August 15, 2013.
6. Kasher, R.; Avneri, S.; Lutsky, M. Y.; Zhang, J.; Gellman, S. H.; Stahl, S. S. Immobilization of Antimicrobial Polymers on RO Membrane to Reduce Biofilm Growth and Biofouling. International Patent Application WO 2012/172547 A1, December 20, 2012.
5. Gerken, J. B.; Stahl, S. S. Cobalt Oxyfluoride Catalysts for Electrolytic Dissociation of Water. US Patent 8192609 B2, June 5, 2012.
4. Smith, C. B.; Kissounko, D. A.; Gellman, S. H.; Stahl, S. S. Catalytic Metathesis of Secondary Amides. US Patent 8039669 B2, October 18, 2011.
3. Stahl, S. S.; Gellman, S. H.; Lee, S. E.; Ilker, M. F.; Weisblum, B.; Kissounko, D. A. Poly-β-Peptides from Functionalized β-Lactam Monomers and Antibacterial Compositions Containing Same. US Patent 7951912 B2, May 31, 2011.
Continuation Patent: US Patent 8519095 B2, August 27, 2013.
Continuation Patent: US Patent 9120892 B2, September 1, 2015.
Continuation Patent: US Patent 9683081 B2, June 20, 2017.
Continuation Patent: US Patent 10323121 B2, June 18, 2019.
2. Stahl, S. S.; Scarborough , C. C. Seven-Membered Heterocyclic Carbenes and their Metal Complexes. US Patent 7750149 B2, July 6, 2010.
Continuation Patent: US Patent 8163900 B2, April 24, 2012.
1. Stahl, S. S.; Gellman, S. H.; Eldred, S. E. Catalytic Transamidation and Amide Metathesis under Moderate Conditions. US Patent 7154004 B2, December 26, 2006.