Palladium-Catalyzed Regioselective Diarylation/Deamination of Homoallylamines: Modular Assembly of 1,1,4,4-Tetraaryl-1,3-butadienes

Abstract

Herein, a novel palladium-catalyzed regioselective diarylation/deamination of homoallylamines is described. During the process, a ubiquitous free amine (NH2) was used as the directing group to accomplish the regioselective δ,δ-diarylation and it was removed in situ to form the privileged 1,1,4,4-tetraaryl-1,3-butadiene motif. This chelate-controlled Heck-type approach eliminates the traditional need of preinstalled and hard removable directing groups, proceeds under simple conditions, and exhibits good tolerance to a wide range of synthetically useful functional groups.