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Journal Article

Reductive Cyclopropanation through Bismuth Photocatalysis

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

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Citation

Ni, S., Spinnato, D., & Cornella, J. (2024). Reductive Cyclopropanation through Bismuth Photocatalysis. Journal of the American Chemical Society, 146(32), 22140-22144. doi:10.1021/jacs.4c07262.


Cite as: https://hdl.handle.net/21.11116/0000-000F-ABEC-7
Abstract
We present here a catalytic method based on a low-valent Bi complex capable of cyclopropanation of double bonds under blue LED irradiation. The catalysis features various unusual Bi-based organometallic steps, namely, (1) two-electron inner sphere oxidative addition of Bi(I) complex to CH2I2, (2) light-induced homolysis of the Bi(III)–CH2I bond, (3) subsequent iodine abstraction-ring-closing, and (4) reduction of Bi(III) to Bi(I) with an external reducing agent to close the cycle. Stoichiometric organometallic experiments support the proposed mechanism. This protocol represents a unique example of a reductive photocatalytic process based on low-valent bismuth radical catalysis.