Nickel metallaphotoredox-catalyzed C–O bond activation/Csp2–Csp3 coupling enabled by phosphine

Abstract

The free alcohol C–O bond activation strategy to generate alkyl radicals, which would serve as a large pool of coupling partners in transition-metal catalysis, remains limited, challenging, and in high demand. Herein, a novel and general nickel/photoredox dual catalysis platform for benzyl alcohol C–O bond activation/Csp²–Csp³ cross coupling of heteroaromatic benzothiazolyl bromide and free benzyl alcohol, enabled by the catalytic generation of an alkyl radical, is reported. The manifold features of this protocol include operational simplicity, high-functional-group tolerance, and broad substrate scope. Notably, late-stage diversification of architecturally intriguing drugs or bioactive molecules further showcases the synthetical potential of this protocol.