Photoredox/Nickel Dual Catalysis for C(sp2)-C(sp3) Cross Electrophile Coupling Reaction Using Phenols and Alcohols as the Latent Electrophile Sources

Abstract

Introducing alkyl groups, particularly through innovative C(sp2)-C(sp3) bond-forming methods utilizing abundant feedstocks, holds promise for expanding chemical diversity, especially in drug discovery programs. Herein, we employed biomass-derived abundant phenols and alkyl alcohols as the coupling partners for the C(sp2)-C(sp3) cross-electrophile coupling reactions. Our innovation involved activating both the coupling partner via the same activator and designing a catalytic system that activates stronger bonds while ensuring coss-selectivity. The visible-light photoredox/nickel dual catalytic systems accommodate large substrate scope tolerating diverse functional groups. Besides, both the activation and cross-coupling reaction could be performed in one pot, and the reaction could be scaled up. Preliminary mechanistic studies involving luminescence quenching, cyclic voltammetry, radical quenching, and radical clock studies elucidated the proposed reaction mechanism.