Tetrahedron Letters | 2019
Brønsted acid-catalyzed radical CH functionalization of acetone with N-allyl anilines to give 3-(3-oxobutyl)indolines
Abstract
Abstract K2S2O8 was unprecedentedly used instead of tert-butyl hydroperoxide (TBHP) in Bronsted acid-assisted catalytic strategy for ketonic radical generation, and the first Bronsted acid-catalyzed radical C H functionalization of acetone across unactivated alkenes is presented. In the presence of TsOH and K2S2O8, N-allyl anilines underwent addition/cyclization cascade with acetone to afford 3-(3-oxobutyl)indolines with exo-selectivity and broad substrate scope at a relatively low temperature.