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.