title: Hydroboration of arynes with N-heterocyclic carbene boranes.
abstract: 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.
authors.affiliation: School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan). tsuyoshi@p.kanazawa-u.ac.jp.
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Taniguchi
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D004583:Electrons; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000480:Alkynes; D001880:Boranes; C030011:carbene; D008697:Methane
keywords: N-heterocyclic carbenes; arynes; boranes; hydroboration; main-group chemistry