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  • Title: Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism.
    Author: Gao Y, Hill DE, Hao W, McNicholas BJ, Vantourout JC, Hadt RG, Reisman SE, Blackmond DG, Baran PS.
    Journal: J Am Chem Soc; 2021 Jun 30; 143(25):9478-9488. PubMed ID: 34128671.
    Abstract:
    One of the most oft-employed methods for C-C bond formation involving the coupling of vinyl-halides with aldehydes catalyzed by Ni and Cr (Nozaki-Hiyama-Kishi, NHK) has been rendered more practical using an electroreductive manifold. Although early studies pointed to the feasibility of such a process, those precedents were never applied by others due to cumbersome setups and limited scope. Here we show that a carefully optimized electroreductive procedure can enable a more sustainable approach to NHK, even in an asymmetric fashion on highly complex medicinally relevant systems. The e-NHK can even enable non-canonical substrate classes, such as redox-active esters, to participate with low loadings of Cr when conventional chemical techniques fail. A combination of detailed kinetics, cyclic voltammetry, and in situ UV-vis spectroelectrochemistry of these processes illuminates the subtle features of this mechanistically intricate process.
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