Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids

Suman Pal, Marine Cotard, Baptiste Gérardin, Christophe Hoarau* and Cédric Schneider*

*Normandy University, University of Rouen, INSA Rouen, CNRS, COBRA UMR 6014, 1 rue Tesnière, 76821 Mont-Saint Aignan Cedex, France, Email: christophe.hoarauinsa-rouen.fr, cedric.schneideruniv-rouen.fr

S. Pal, M. Cotard, B. Gérardin, C. Hoarau, C. Schneider, Org. Lett., 2021, 23, 3130-3135.

DOI: 10.1021/acs.orglett.1c00812

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Abstract

A regioselective oxidative allylic C(sp³)-H arylation of readily available unactivated terminal and internal olefins with a broad range of heteroaryl boronic acids is catalyzed by cheap, abundant, and nontoxic Cu₂O. This method does not require traditional coupling partners with preinstalled leaving groups at the allylic position, thus offering an alternative method to allylic arylation.

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Key Words

allylation, cyclohexenes, cycloheptenes, DTBP

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ID: J54-Y2021