1,2-Migration of N-Diarylboryl Imidazol-2-ylidene through Intermolecular Radical Process
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Updated: Oct 1, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Wei-Chun Liu1, Yi-Hung Liu1, Tien-Sung Lin1
1Department of Chemistry, National Taiwan University , No. 1, Section 4, Roosevelt Road, Taipei 10617, Taiwan.
Abstract:
1,2-Boryl migration of N-boryl N-heterocyclic carbene to 2-boryl imidazole is proposed to proceed through generation and recombination of two radical intermediates, namely, a neutral diarylboron radical and a N-heterocyclic carbene radical. Crossover experiments suggest that these two radical species are stable enough to escape solvent cages and recombine intermolecularly. The presence of radical intermediates is further supported by spin trapping experiments. Besides, the coordination of Li+ cation is found to be critical for the stability of the NHC radical.
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