Photoredox/nickel dual-catalyzed regio- and stereo-selective cross-coupling of allyl trifluoroborates with alkenyl electrophiles: synthesis of 1,4-dienes

Abstract

A mild photoredox/nickel dual-catalyzed cross-coupling of allyl trifluoroborates with vinyl bromides or -triflates has been developed. This catalytic protocol allows direct and efficient synthesis of 1,4-dienes with generally good to high yields, high regio- and stereo-selectivity, and wide substrate scope and functional group compatibility. The double bond configuration in both allyl trifluoroborates and vinyl bromides could be preserved, providing a practical means for 1E,4E-diene synthesis.