Electrochemical generation of NHC-boryl radicals for carbon-centered radical formation

Ligated boryl radicals have emerged as versatile open-shell intermediates for bond construction, yet their deployment in electrosynthesis remains underdeveloped relative to thermal peroxide-initiated and photoredox-enabled methods. Herein, we report the anodic generation of NHC-ligated boryl radicals using inexpensive graphite electrodes and demonstrate their utility across multiple radical manifolds, including (i) radical decyanation, (ii) decyanative alkylation, and (iii) a Giese-type reductive radical hydroalkylation. The nature of borane-electrode interaction has been elucidated through in-depth cyclic voltammetry analysis. The reliability of the methodology is demonstrated by its smooth scalability across various continuous-flow reactor systems, including a parallel-plate reactor and a Spinning Cylinder Electrochemical Reactor.