Pd(PPh3)4-Catalyzed Regioselective C–H para-Allylation of N,N-Dialkylanilines using Vinyl Benzoxazinanones

Abstract

A Pd(PPh3)4-catalyzed regioselective C–H para allylation process was developed for the reaction of N,N-dialkylanilines with vinyl benzoxazinanones. Such transformation demonstrated a novel application of vinyl benzoxazinanone reagents, allowing for the introduction of an alkenyl group exclusively to the para position of aniline derivatives. As a result, a series of N,N-dialkylaniline derivatives with para allyl type substitutions were synthesized with excellent regioselectivities (E:Z ratio >19:1).