Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 48, Pages 13150-13154Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408345
Keywords
arynes; boranes; hydroboration; main-group chemistry; N-heterocyclic carbenes
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT)
- US National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1265652] Funding Source: National Science Foundation
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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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