Nickel-catalyzed oxidative fluoroalkylation of aryl halides via paired electrolysis

Abstract

The paired electrolysis triggers multiple oxidative and reductive processes to occur simultaneously, which ensures the steady transformation of the intermediates to the desired coupling products. However, fluoroalkyl radicals have not been harnessed for metal-catalyzed cross-coupling with aryl halides under electrochemical conditions. This work describes a general strategy for rapid access to various fluoromethyl and difluoromethyl aromatics by paired electrolysis. The contradiction between anodic oxidation of fluoroalkyl sulfinates and cathodic reduction of low-valent nickel catalysts can be well addressed under mild cell conditions, allowing for direct introduction of fluorinated functionalities into aromatic systems.

Electrochemical-Promoted Nickel-Catalyzed Oxidative Fluoroalkylation of Aryl Iodides

“…Further studies in electrochemical fluoroallylation are underway in our laboratory. 18 ■ ASSOCIATED CONTENT * sı Supporting Information…”

“…The paradox between anodic oxidation of fluoroalkyl sulfinates and cathodic generation of low-valent nickel species can be conciliated under mild cell conditions, which is difficult to proceed in batch reaction with chemical oxidants. Further studies in electrochemical fluoroallylation are underway in our laboratory …”