Herein we report a nickel-catalyzed decarboxylative Csp3-Csp2 coupling reaction under electrochemical conditions. The reaction is involves single electron transfer (SET) from the electrode surface to an N-hydroxyphthalimide ester which enters the nickel catalytic cycle after decarboxylative fragmentation. A SET event to nickel from the electrode following reductive elimination of the coupling product closes the catalytic cycle. A tertiary amine is employed as the terminal reductant instead of a traditionally employed metal powder. The reaction exhibits good substrate generality and functional group compatibility with respect to both coupling partners. Optimization of the reaction under continuous flow conditions improved both chemoselectivity and yield of desired coupling product.

Nickel-catalyzed decarboxylative Csp3-Csp2 reductive couplings under electrochemical conditions in batch and continuous flow

256th National Meeting (2018)

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