Precise electro-reduction of alkyl halides for radical defluorinative alkylation

Science China Chemistry(2022)

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Abstract
Reported here is a precise electro-reduction strategy for radical defluorinative alkylation towards the synthesis of gem -difluoroalkenes from α-trifluoromethylstyrenes. According to the redox-potential difference of the radical precursors, direct or indirect electrolysis is respectively adopted to realize the precise reduction. An easy-to-handle, catalyst- and metal-free condition is developed for the reduction of alkyl radical precursors that are generally easier to be reduced than α-trifluoromethylstyrenes, while a novel electro-Ni-catalytic system is established for the electro-reduction of alkyl bromides or chlorides towards the electrochemical synthesis of gem -difluoroalkenes. The merit of this protocol is exhibited by its mild conditions, wide substrate scope, and scalable preparation. Mechanistic studies and DFT calculations proved that the coordination of α-trifluoromethylstyrenes to Ni-catalyst prevents the direct reduction of the alkene and, in turn, promotes the activation of alkyl bromide through halogen atom transfer mechanism.
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Key words
electro-reductive cross-coupling,gem-difluoroalkenes,radical defluorinative alkylation,electro/nickel catalysis,C-C bonds formation
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