Journal of the American Chemical Society, Vol.139, No.31, 10657-10660, 2017
Nickel-Catalyzed beta,gamma-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 beta,gamma-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(sp(3))-C(sp(3)) reductive elimination step.