Recently, electrochemistry has emerged as an attractive tool for organic synthesis, since the replacement of stoichiometric amounts of chemical reagents or oxidants in conventional synthesis methods with electrons as a mass-free reagent can minimize waste dramatically. Consequently, electrochemical synthesis has been identified as an environmentally benign and powerful synthetic strategy to form various C-C and C-X (X = heteroatom) bonds.<br/>As a part of our efforts to continuously develop cheap and green C-X (X = heteroatom) bond formation transformations, we envision that electrochemical deborylative functionalization of readily accessible arylboronic acids could selectively occur employing electricity as the driving force. As exhibited in Scheme 1, metal-free electrocatalytic deborylative halogenation of diverse arylboronic acids has been reported to synthesize aryl halides under mild conditions (route a), electrochemical deborylative seleno/thiocyanation has been established to prepare corresponding aryl seleno/thiocyanates (route b), constructing aryl selenoethers through deborylative selenylation of arylboronic acids has been realized in the absence of metal catalyst and external oxidant (route c), an economical electrochemical deborylative <i>ipso</i>-hydroxylation has been achieved to build various arenols under aerobic conditions (route d). The protocols are compatible with diverse substitution patterns on the aryl ring of the phenylboronic acid including a broad range of electron-withdrawing and -donating functional groups, whose synthetic application has been highlighted through scale-up experiments in galvanostatic mode. Cyclic voltammetry experiments have indicated that the coupling partners were oxidized prior to the arylboronic acid substrate under electrochemical conditions.

Electrochemical method for metal-free deborylative functionalization of arylboronic acids

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