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Journal Article

Bi-Catalyzed Trifluoromethylation of C(sp2)–H Bonds under Light

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Tsuruta,  Takuya
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Spinnato,  Davide
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Moon,  Hye Won
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch,  Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cornella,  Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Tsuruta, T., Spinnato, D., Moon, H. W., Leutzsch, M., & Cornella, J. (2023). Bi-Catalyzed Trifluoromethylation of C(sp2)–H Bonds under Light. Journal of the American Chemical Society, 145(47), 25538-25544. doi:10.1021/jacs.3c10333.


Cite as: https://hdl.handle.net/21.11116/0000-000D-FBDD-0
Abstract
We disclose a Bi-catalyzed C–H trifluoromethylation of (hetero)arenes using CF3SO2Cl under light irradiation. The catalytic method permits the direct functionalization of various heterocycles bearing distinct functional groups. The structural and computational studies suggest that the process occurs through an open-shell redox manifold at bismuth, comprising three unusual elementary steps for a main group element. The catalytic cycle starts with rapid oxidative addition of CF3SO2Cl to a low-valent Bi(I) catalyst, followed by a light-induced homolysis of Bi(III)–O bond to generate a trifluoromethyl radical upon extrusion of SO2, and is closed with a hydrogen-atom transfer to a Bi(II) radical intermediate.