Hydroboration of Arynes with N‐Heterocyclic Carbene Boranes
Identifieur interne : 004932 ( Main/Exploration ); précédent : 004931; suivant : 004933Hydroboration of Arynes with N‐Heterocyclic Carbene Boranes
Auteurs : Tsuyoshi Taniguchi [Japon, États-Unis] ; Dennis P. Curran [États-Unis]Source :
- Angewandte Chemie [ 0044-8249 ] ; 2014-11-24.
Abstract
Arynes were generated in situ from ortho‐silyl aryl triflates and fluoride ions in the presence of stable N‐heterocyclic carbene boranes (NHCBH3). Spontaneous hydroboration ensued to provide stable B‐aryl‐substituted NHC‐boranes (NHCBH2Ar). 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.
Url:
DOI: 10.1002/ange.201408345
Affiliations:
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Spontaneous hydroboration ensued to provide stable B‐aryl‐substituted NHC‐boranes (NHCBH2Ar). 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. 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