Nickel-catalyzed reductive 1,2-alkylarylation of alkenes via a 1,5-hydrogen atom transfer (HAT) cascade

Abstract

N-centered radical-mediated remote C(sp³)–H functionalization via HAT processes has been successfully applied in the difunctionalization of alkenes, serving as an elegant and robust method to convert readily available alkenes into various functionalized molecules. However, HAT strategy-enabled difunctionalization of alkenes using electrophiles as functionalizing reagents remains underexplored. In this study, we report a nickel-catalyzed regioselective reductive three-component 1,2-alkylarylation of alkenes with O-oxalate hydroxamic acid esters and aryl iodides. This radical addition/cross-coupling cascade reaction involves amidyl radical-triggered intramolecular 1,5-HAT and nickel-catalyzed reductive coupling processes under mild reaction conditions with good coupling efficiency. Additionally, this approach can be extended to the reductive 1,2-alkylarylation of alkynes, providing an efficient method for the synthesis of multi-substituted alkenes from easily accessible starting materials.