Remote Migratory Reductive Arylation of Unactivated Alkenes Enabled by Electrochemical Nickel Catalysis

ChemSusChem. 2024 Oct 29:e202402196. doi: 10.1002/cssc.202402196. Online ahead of print.

Abstract

Transition metal-catalyzed cross-coupling reaction between organometallic reagents and electrophiles is a potent method for constructing C(sp2)-C(sp3) bonds. Given the characters of organometallic reagents, cross-reductive coupling is emerging as an alternative strategy. The resurgence of electrochemistry offers an ideal method for electrochemical reductive of cross-coupling electrophiles. Inspired by the mechanism of electrochemical metal hydride, our study proposed that Ni-H electrochemically catalyze the hydroarylation coupling of unactivated alkenes with aryl halides. 1,1-Diarylalkanes can be produced effectively. This method have advantages including mild conditions, excellent regioselectivity, and satisfactory yields.

Keywords: Alkene; Aryl bromide; Cross-coupling; Electrochemistry; Nickel catalyst.