Ring-opening silylation of N-arylindoles via endocyclic C–N bond cleavage triggered by silylboranes

Abstract

The cleavage of heteroaromatic endocyclic carbon–heteroatom bonds to assemble C–Si bonds is scarce. Here, we demonstrate an unprecedented dearomatization silylation of N-arylindoles arising from reductive activation initiated by electron-rich silylboronic complexes to deliver silyl styrenes with perfect stereoselectivity.