Selective and efficient synthesis of trans-arylvinylboronates and trans-hetarylvinylboronates using palladium catalyzed cross-coupling

Abstract

trans-Arylvinylboronate derivatives are important synthesis blocks in natural products, pharmaceuticals and organic materials. There are only a few reaction conditions that could selectively provide trans-arylvinylboronates by Heck coupling of pinacol vinylboronate and aryl halides. Here we report an efficient and versatile method of palladium catalyzed cross-coupling between pinacol vinylboronate and various aryl or hetaryl bromides to obtain the corresponding trans-(het)arylvinylboronates in excellent yields and selectivity. 30 examples have been synthesized using this protocol which offers an alternative method to prepare these useful building blocks.