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 into the para-position of aniline derivatives. As a result, a series of N,N-dialkylaniline derivatives with para-allyl type substituents were synthesized with excellent regioselectivities (E : Z ratios >19 : 1).