Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines

We disclose a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in y,(5-alkenylketimines with aryl halides and arylketones with the construction of two C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. Electron-deficient alkenes play crucial dual roles as ligands to stabilize reaction intermediates and to increase catalytic rates for the formation of C(sp3)-C(sp3) bonds. This alkene alkylarylation reaction is also effective for secondary alkylzinc reagents and internal alkenes and proceeds with a complete regio- and stereocontrol, affording products with up to three contiguous all-carbon all-cis secondary stereocenters.

Automated summary

We have disclosed a novel Ni-catalyzed alkylarylation reaction of electron-deficient alkenes, which allows the construction of two carbon-carbon bonds. The electron-deficient alkenes play a crucial role in stabilizing reaction intermediates and enhancing the catalytic rates. This reaction is also applicable to secondary alkylzinc reagents and internal alkenes, and exhibits excellent regio- and stereocontrol, leading to products with up to three contiguous all-carbon all-cis secondary stereocenters.