Nickel-Catalyzed Three-Component 1,1-Difunctionalization of Unactivated Alkenes with Quinoxaline/Naphthoquinone and Arylboronic Acids via Organometallic-Radical Relay

A nickel-catalyzed intermolecular three-component 1,1-difunctionalization
of unactivated alkenes with quinoxaline/naphthoquinone and arylboronic
acids via organometallic-radical relay is developed. This efficient
protocol provides a new method to access a variety of arylalkanes
in moderate to good yields with a broad substrate scope and excellent
functional group tolerance. The mechanistic studies provide insights
into the mechanism and origin of chemo- and regioselectivity as well
as confirm the generation of functionalized benzylic radicals.