Advances in chemistry of N-heterocyclic carbene boryl radicals

Boron-centred radicals (boryl radicals) are potential and attractive species in main group chemistry and synthetic chemistry. Recently, the development of boron compounds ligated by N-heterocyclic carbenes (NHCs) has sparked off advavnces in boryl radical chemistry because NHCs can highly stabilise boryl radicals by electronic and steric factors. This review highlights recent synthesis and reactions of such NHC-boryl radicals. From the standpoint of main group chemistry, examples of isolation or detection of unique NHC-boryl radicals are presented. From the standpoint of synthetic chemistry, on the other hand, the development of reactions of user-friendly NHC-boryl radicals, which has contributed to radical chemistry, organoboron chemistry and polymer science, is comprehensively described.