Stahl, Shannon S. - University of Wisconsin-Madison

个人简介

NSF Postdoctoral Fellow (1997 – 1999)Massachusetts Institute of Technology, Cambridge, MA Advisor: Professor Stephen J. Lippard Mechanistic Enzymology of Soluble Methane Monooxygenase Ph.D. Chemistry (1997)NSF Predoctoral Fellow California Institute of Technology, Pasadena, CA Advisor: Professor John E. Bercaw Thesis: Mechanistic Studies of Alkane Activation by Platinum(II) Complexes B.S. Chemistry (1992)University of Illinois at Urbana-Champaign, Urbana, IL

研究领域

Catalytic Oxidation with Molecular Oxygen Catalytic Radical C–H Oxidation and Cross-Coupling Catalytic Methods for Biomass Conversion and Valorization Electrocatalysis and Electrochemical Organic Synthesis Electrocatalysts and Electrochemical Energy Storage and Conversion

近期论文

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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. DOI: 10.1016/j.chempr.2024.04.001 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. DOI: 10.1021/acssuschemeng.3c08032. Preprint. 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. DOI: 10.1021/acs.iecr.3c04466. Preprint. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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.