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Hydroboration of Arynes with N‐Heterocyclic Carbene Boranes
Author(s) -
Taniguchi Tsuyoshi,
Curran Dennis P.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408345
Subject(s) - boranes , hydroboration , aryne , chemistry , carbene , borane , aryl , medicinal chemistry , silylation , hydride , organic chemistry , boron , catalysis , metal , alkyl
Arynes were generated in situ from ortho ‐silyl aryl triflates and fluoride ions in the presence of stable N‐heterocyclic carbene boranes (NHCBH 3 ). Spontaneous hydroboration ensued to provide stable B‐aryl‐substituted NHC‐boranes (NHCBH 2 Ar). 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.