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Reductive Cross-Coupling of Olefins via a Radical Pathway

[Image: see text] 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....

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Detalles Bibliográficos
Autores principales: Zhou, Wei, Dmitriev, Igor A., Melchiorre, Paolo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10682986/
https://www.ncbi.nlm.nih.gov/pubmed/37947488
http://dx.doi.org/10.1021/jacs.3c11285
Descripción
Sumario:[Image: see text] 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 sp(3)-dense molecules from olefins using an unconventional disconnection.