Regioselective palladium-catalyzed synthesis of beta-arylated primary allylamine equivalents by an efficient Pd-N coordination

A highly regioselective Heck arylation, utilizing aryl triflates and a pall adium/dppf catalytic system, can be performed at the internal, beta -carbon of Boc- and phthalimido-protected allylamines, yielding arylated primary a llylamine equivalents. The very high regioselectivity obtained with seconda ry Boc-protected allylamides is suggested to be caused by an efficient coor dination between an anionic nitrogen and palladium. Single-mode microwave i rradiation has been utilized to shorten the reaction times and, in the case of Boc-protected allylamides, to improve the yields of two electron-poor a ryl triflates.