Remote C(sp3)–H vinylation via radical-mediated consecutive fission of C–H and C–C bonds

Abstract

Described herein is a radical-mediated vinylation of the remote C(sp³)–H bonds of propargylic alcohols. A variety of widely available reagents, such as acetonitrile, ethers, aliphatic alcohols, and simple alkanes, serve as both the solvent and coupling partner. The transformation proceeds via sequential vinyl radical-mediated HAT and intramolecular vinyl migration, in which two inert C(sp³)–H bonds and one C–C bond are homolysed. The reaction also features broad functional group tolerance, good regio-/chemo-selectivity, and synthetic step-economy.