Regioselective nickel-catalyzed dicarbofunctionalization of unactivated alkenes enabled by picolinamide auxiliary
Shenghao Wang, Chun Luo, Lei Zhao, Junsong Zhao, Lanlan Zhang, Bolin Zhu, Chao Wang
Abstract
Catalytic difunctionalization of alkenes has been a prominent research theme in recent years. Here, we develop a removable bidentate picolinamide-assisted regioselective dicarbofunctionalization of homoallylic amines with organohalides and arylboronic acids. The catalytic system, using cost-effective and air-stable Ni(II) precatalyst, which could be activated by arylboronic acids, provides access to the regioselective diarylation and arylalkylation of unactivated alkenes. This reaction is compatible with α- or β-substituted terminal alkenes and internal alkenes and exhibits excellent functional group and heterocycle tolerance. Preliminary mechanistic studies suggest that the reaction proceeds via a NiI/NiIII catalytic cycle rather than a Ni0/NiII cycle. Notably, the general and practical protocol developed herein represents, to the best of our knowledge, the first example of Ni-catalyzed 3-component 2,1-diarylation and arylalkylation of alkenes with arylboronic acids and organohalides.