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Activation and C‒C Coupling of Aryl Iodides via Bismuth Photocatalysis

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Mato,  Mauro
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Stamoulis,  Alexios
Research Group Cornellà, 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

Mato, M., Stamoulis, A., Bruzzese, P. C., & Cornella, J. (2024). Activation and C‒C Coupling of Aryl Iodides via Bismuth Photocatalysis. Angewandte Chemie International Edition, e202418367. doi:10.1002/anie.202418367.


Cite as: https://hdl.handle.net/21.11116/0000-0010-021B-E
Abstract
Within the emerging field of bismuth redox catalysis, the catalytic formation of C‒C bonds using aryl halides would be highly desirable; yet such a process remains a synthetic challenge. Herein, we present a chemoselective bismuth-photocatalyzed activation and subsequent coupling of (hetero)aryl iodides with pyrrole derivatives to access C(sp2)‒C(sp2) linkages through C‒H functionalization. This unique reactivity is the result of the bismuth complex featuring two redox state-dependent interactions with light, which 1) activates the Bi(I) complex for oxidative addition via MLCT, and 2) promotes the homolytic cleavage of aryl Bi(III) intermediates through a LLCT process.