Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling

A nickel-catalyzed conjunctive cross-coupling between non-conjugated alkenes, aryl iodides, and alkyl­zinc reagents is reported. Excellent regio­control is achieved utilizing an 8-amino­quinoline directing group that can be readily cleaved to unmask net β,γ-dicarbo­functionalized carboxylic acid products. Under optimized conditions, both terminal and internal alkene substrates provided the corresponding alkyl/aryl difunctionalized products in moderate to excellent yields. The methodology developed herein represents the first three-component 1,2-dicarbofunctionalization of non-conjugated alkenes involving a C­(sp3)–C­(sp3) reductive elimination step.