Organo-photocatalytic dearomative hydrosilylation of indoles with silanes

Abstract

A photocatalytic dearomative hydrosilylation reaction of indole derivatives with silanes has been accomplished for the synthesis of valuable indolinyl silanes through a carbon-silyl radical coupling process with the cooperation of photoredox and hydrogen atom transfer catalytic systems composed of 3DPA2FBN (2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile), (i-Pr)₃SiSH, and base additives. This protocol is featured by a broad substrate scope, transition metal-free conditions, high diastereoselectivities and applications in natural product derivatives.