1,4-Aminoarylation of Butadienes via Photoinduced Palladium Catalysis.

Abstract

A visible-light-induced, three-component palladium-catalyzed 1,4-aminoarylation of butadienes with readily available aryl halides and aliphatic amines has been developed, affording allylamines with excellent E-selectivity. The reaction exhibits exceptional control over chemo-, regio-, and stereoselectivity, a broad substrate scope, and high functional group compatibility, as demonstrated by the late-stage functionalization of bioactive molecules. Mechanistic investigations are consistent with a photoinduced radical Pd(0)-Pd(I)-Pd(II)-Pd(0) Heck-Tsuji-Trost allylation cascade.