Copper-catalyzed enantioselective arylalkynylation of alkenes

Chem Sci. 2020 Jan 8;11(6):1623-1628. doi: 10.1039/c9sc04029c. eCollection 2020 Feb 14.

Abstract

A copper-catalyzed enantioselective arylalkynylation of alkenes with diaryliodonium salt and a monosubstituted alkyne is reported. The three-component coupling reactions proceed under mild reaction conditions with a broad substrate scope, leading to synthetically valuable 1,2-diaryl-3-butynes. The key to the success of this chemistry is the employment of the chiral bisoxazoline-phenylaniline (BOPA) ligand. A novel reaction pathway involving the phenyl radical generation under thermal copper catalysis is proposed according to mechanistic studies.