Palladium-catalysed cyclisation–amination of allenes-effect of base on regioselectivity of formation of allylic amines

Abstract

The palladium catalysed cyclisation of aryl iodides onto proximal allenes occurs at the centre carbon atom of the allene forming a five- or six-membered rings and generating a π-allyl intermediate. The regiochemistry of attack of secondary amines on the π-allyl intermediate is sensitive to added inorganic base, steric effects and the nature of the adjacent heteroatom.