Yoon, Tehshik P. - University of Wisconsin-Madison

个人简介

Professional Experience Professor of Chemistry 2013–present Associate Professor of Chemistry 2011–2013 Assistant Professor of Chemistry 2005–2011 University of Wisconsin–Madison University of California–Berkeley, Department of Chemistry (Berkeley, CA) 1998–1999 Lecturer: Organic chemistry Merck Research Laboratories (Rahway, NJ) 1994 Summer intern/research assistant: Synthetic organic chemistry Education and Training Postdoctoral Fellow (NIH) 2002–2005 Harvard University, Cambridge, MA Advisor: Professor Eric N. Jacobsen Ph.D., Chemistry California Institute of Technology, Pasadena, CA 2000–2002 University of California, Berkeley, CA 1999–2000 Advisor: Professor David W. C. MacMillan Thesis: The Acyl-Claisen Rearrangement. Development of a Novel Metal-Catalyzed Claisen Rearrangement and Enantioselective Variants of the Acyl-Claisen Rearrangement. M.S., Chemistry 1996–1998 California Institute of Technology, Pasadena, CA Advisor: Professor Erick M. Carreira Thesis: Studies Towards the Total Synthesis of Welwitindolinone A Isonitrile. A.B., Chemistry (summa cum laude) 1992–1996 Harvard University, Cambridge, MA Advisor: Prof. David. A. Evans

研究领域

Research in the Yoon group focuses on the development of new reaction methods for organic synthesis. We are particularly interested in the use of catalysis as a strategy for increasing process efficiency, controlling reaction selectivity, and reducing the environmental impact of chemical synthesis. Representative project areas include the following. Visible Light Photocatalysis. Photochemical reactions are intriguing from a synthetic perspective because the stereochemistry, regiochemistry, and chemoselectivity of organic reactions can differ dramatically under conditions of either thermal or photochemical activation. Yet organic chemists have long been reluctant to use photochemical reactions in complex molecule synthesis, and the properties of the structures that are uniquely accesible using photochemical activation have thus been relatively unexplored. A central goal of our research is to develop photochemical methods that can conveniently be conducted by any synthetic organic chemist, using sources of visible light that are already present in a standard chemistry lab. We focus upon the photoactivity of the transition metal chromophores that have been extensively exploited in the design of technologies for solar energy conversion. We have shown that complexes such as Ru(bpy)32+ and its derivatives can also be used to photochemically activate organic molecules towards a wide range of synthetically useful transformations.

近期论文

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Li, Q.Y., Gockel, S.N., Lutovsky, G.A., DeGlopper, K. S.; Baldwin, N. J.; Bundesmann, M. W.; Tucker, J. W.; Bagley, S. W.; Yoon, T. P. Decarboxylative cross-nucleophile coupling via ligand-to-metal charge transfer photoexcitation of Cu(II) carboxylates. Nat. Chem. 2022 in press. Genzink, M. J.; Kidd, J. B.; Swords, W. B.; Yoon, T. P. Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis, Chem. Rev. 2021, in press. Sherbrook, E. M.; Genzink, M. J.; Park, B.; Guzei, I. A.; Baik, M.-H.; Yoon, T. P. Chiral Brønsted acid-controlled intermolecular asymmetric [2 + 2] photocycloadditions, Nat. Commun. 2021, 12, 5735. Dong, X.; Li, Q. Y.; Yoon, T. P. Enantioselective Synthesis of γ-Oxycarbonyl Motifs by Conjugate Addition of Photogenerated α-Alkoxy Radicals, Org. Lett. 2021, 23, 5803–5708. Cahoon, S. B.; Yoon, T. P., Photochemistry and Radical Generation: Approaches in Mechanism Elucidation. In Science of Synthesis: Free Radicals: Fundamentals and Applications in Organic Synthesis, Fensterbank, L.; Ollivier, C., Eds.; Thieme: Stuttgart, (2021); Vol. 1, p 159-205. Reed, N. L.; Lutovsky, G. A.; Yoon, T. P. Copper-Mediated Radical–Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes, J. Am. Chem. Soc. 2021, 143, 6065–6070. Scholz, S. O.; Kidd, J. B.; Capaldo, L.; Flikweert, N. E.; Littlefield, R. M.; Yoon, T. P. Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters, Org. Lett. 2021, in press. Reed, N. L.; Yoon, T. P. Oxidase Reactions in Photoredox Catalysis, Chem. Soc. Rev. 2021, 50, 2954–2967. Gravatt, C. S.; Melecio-Zambrano, L.; Yoon, T. P. Olefin-Supported Cationic Copper Catalysts for Photochemical Synthesis of Structurally Complex Cyclobutanes, Angew. Chem. Int. Ed. 2021, 60, 3989–3993. Zheng, J.; Dong, X.; Yoon, T. P. Divergent Photocatalytic Reactions of α-Ketoesters under Triplet Sensitization and Photoredox Conditions, Org. Lett. 2020, 16, 6520–6525. Skubi, K. L.; Swords, W. B.; Hofstetter, H.; Yoon, T. P. LED‐NMR Monitoring of an Enantioselective Catalytic [2+2] Photocycloaddition, ChemPhotoChem 2020, 4, 685–690. Sherbrook, E. M.; Jung, H.; Cho, D.; Baik, M. H.; Yoon, T. P. Brønsted Acid Catalysis of Photosensitized Cycloadditions, Chem. Sci. 2020, 11, 856–861. Lee, B. J.; DeGlopper, K. S.; Yoon, T. P. Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis. Angew. Chem. Int. Ed. 2020, 59, 197–202. Yoon, T. P. Stereocontrolled Photochemical Synthesis. ChemPhotoChem 2019, 3, 1201–1202. Zheng, J.; Swords, W. B.; Jung, H.; Skubi, K. L.; Kidd, J. B.; Meyer, G. J.; Baik, M.-H.; Yoon, T. P. Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis. J. Am. Chem. Soc. 2019, 141, 13625–13634. [cover] Daub, M. E.; Jung, H.; Lee, B. J.; Won, J.; Baik, M. H.; Yoon, T. P. Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer. J. Am. Chem. Soc. 2019, 141, 9543–9547. Amador, A. G.; Sherbrook, E. M.; Yoon, T. P. A Redox Auxiliary Strategy for Pyrrolidine Synthesis via Photocatalytic [3+2] Cycloaddition. Asian J. Org. Chem. 2019, 8, 978–985. Sherbrook, E. M.; Yoon, T. P. Asymmetric Catalysis of Triplet-State Photoreactions. Photochemistry 2019, 46, 432-448. Farney, E. P.; Chapman, S. J.; Swords, W. B.; Torelli, M. D.; Hamers, R. J.; Yoon, T. P. Discovery And Elucidation Of Counteranion Dependence in Photoredox Catalysis. Journal of the American Chemical Society 2019, 141, 6385-6391. Reed, N. L.; Herman, M. I.; Miltchev, V. P.; Yoon, T. P. Tandem Copper and Photoredox Catalysis in Photocatalytic Alkene Difunctionalization Reactions. Beilstein J. Org. Chem. 2019, 15, 351–356.