Heterocyclization, deprotection and isomerization in an intramolecular palladium-catalysed tertiary amine–allyl coupling reaction

Abstract

N-Methyl-N-allyl-2-(1-acetoxyallyl)benzylamine reacts in the presence of tetrakis(triphenylphosphine)palladium to afford a mixture of an isoindole, a 2-benzazepine and allyl acetate; the likely reaction pathway involves a multistep procedure whereby each Pd atom is implicated at least four times, the formation of the isoindole occuring first, followed by an isomerisation to the benzazepine derivative.