KOt-Bu-mediated transition-metal-free indole synthesis

Abstract

A single-electron transfer (SET)-mediated modular indole formation reaction from a 2-iodoaniline and a ketone has been developed. This transition metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the facile product formation and regiocontrol are governed by the internal metal coordination and torsional strain of the radical intermediates.