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Hydroboration of arynes with N-heterocyclic carbene boranes



Hydroboration of arynes with N-heterocyclic carbene boranes



Angewandte Chemie 53(48): 13150-4



Arynes were generated in situ from ortho-silyl aryl triflates and fluoride ions in the presence of stable N-heterocyclic carbene boranes (NHC-BH3). Spontaneous hydroboration ensued to provide stable B-aryl-substituted NHC-boranes (NHC-BH2Ar). The reaction shows good scope in terms of both the NHC-borane and aryne components and provides direct access to mono- and disubstituted NHC-boranes. The formation of unusual ortho regioisomers in the hydroboration of arynes with an electron-withdrawing group supports a hydroboration process with hydride-transfer character.

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Accession: 053620541

Download citation: RISBibTeXText

PMID: 25346015

DOI: 10.1002/anie.201408345


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