NHC induced radical formation via homolytic cleavage of B-B bonds and its role in organic reactions.

ABSTRACT: New borylation methodologies have been reported recently, wherein diboron(4) compounds apparently participate in free radical couplings via the homolytic cleavage of the B-B bond. We report herein that bis-NHC adducts of the type (NHC)₂·B₂(OR)₄, which are thermally unstable and undergo intramolecular ring expansion reactions (RER), are sources of boryl radicals of the type NHC-BR₂˙, exemplified by Me₂Im^Me·Bneop˙ 1a (Me₂Im^Me = 1,3,4,5-tetramethyl-imidazolin-2-ylidene, neop = neopentylglycolato), which are formed by homolytic B-B bond cleavage. Attempts to apply the boryl moiety 1a in a metal-free borylation reaction by suppressing the RER failed. However, based on these findings, a protocol was de

SUBMITTER: Kuehn L 

PROVIDER: S-EPMC9297536 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature