Olefins are widely available at low costs, which explains the usefulness of developing new methods for their functionalization. Here we report a simple protocol that uses a photoredox catalyst and an inexpensive thiol catalyst to stitch together two olefins, forming a new C-C bond. Specifically, an electron-poor olefin is reduced by the photoredox catalyst to generate, upon protonation, a carbon radical, which is then captured by a neutral olefin. This intermolecular cross-coupling process provides a tool for rapidly synthesizing sp3-dense molecules from olefins using an unconventional disconnection.

Zhou, W., Dmitriev, I.A., Melchiorre, P. (2023). Reductive Cross-Coupling of Olefins via a Radical Pathway. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 145(46), 25098-25102 [10.1021/jacs.3c11285].

Reductive Cross-Coupling of Olefins via a Radical Pathway

Melchiorre, Paolo
Supervision
2023

Abstract

Olefins are widely available at low costs, which explains the usefulness of developing new methods for their functionalization. Here we report a simple protocol that uses a photoredox catalyst and an inexpensive thiol catalyst to stitch together two olefins, forming a new C-C bond. Specifically, an electron-poor olefin is reduced by the photoredox catalyst to generate, upon protonation, a carbon radical, which is then captured by a neutral olefin. This intermolecular cross-coupling process provides a tool for rapidly synthesizing sp3-dense molecules from olefins using an unconventional disconnection.
2023
Zhou, W., Dmitriev, I.A., Melchiorre, P. (2023). Reductive Cross-Coupling of Olefins via a Radical Pathway. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 145(46), 25098-25102 [10.1021/jacs.3c11285].
Zhou, Wei; Dmitriev, Igor A; Melchiorre, Paolo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/949613
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