Abstract
The oxidative Heck reaction of strongly coordinating heterocycles with internal olefins often led to elusive reactivity and regioselectivity. Herein, by judicious choice of X-type directing groups under Ru(ii) catalysis, we achieved the regioselective oxidative Heck reaction of strongly coordinating heterocycles with sterically demanding internal olefins. It was postulated that the "match/mismatch effect" of sterically demanding internal olefins as coupling partners and subsequent kinetically favoured Michael addition or oxidative aromatization act as driving forces to facilitate the desired reactivity and site-selectivity.