A chemoselective radical cascade polarity-mismatched silylarylation of unactivated alkenes†

Abstract

Here, we report a practical method to selectively access silylated pyrrolo[1,2-a]indoles using alkenyl indoles and readily available silanes through a radical cascade cyclization. The reaction proceeds through an unusual intermolecular polarity-mismatched addition of a nucleophilic silyl radical to e-rich alkene SOMOphiles via a coordination-assisted interaction. The scope and functional group compatibility of the protocol as well as a detailed mechanistic investigation are presented.