Nickel-Catalyzed Cross-Electrophile Vinyl–Vinyl Coupling: An Approach to Structurally Versatile Dienylboronates
Guangli Xu, Chunyan Liu, Xiaobo Pang, Xue‐Yuan Liu, Xing‐Zhong Shu
Abstract
Cross C-C bond formation of two vinyl electrophiles is a long-standing challenge in synthetic chemistry. Herein, we report a nickel-catalyzed reductive vinyl-vinyl coupling between vinyl triflates and boron-substituted vinyl bromides. This new protocol offers facile access to dienylboronates with high structural complexity and molecular diversity. The reaction proceeds with a broad substrate scope under very mild conditions. The synthetic utility of the method is highlighted by its gram-scale reaction, modification of complex molecules, and diverse transformation of the products. [GRAPHICS] .
Topics & Concepts
ElectrophileChemistryMaterial chemistryOrganic chemistryGreen chemistryCatalysisReaction mechanismCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods