1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N‑Heterocyclic Carbene Boranes

Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron-poor aromatic rings under photoredox conditions provide dearomatized 3-NHC-boryl-1,5-cycohexadienes, which are formally products of 1,4-hydroboration reactions. When regioisomers are possible, the more crowded (doubly ortho-subs...

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Published inJournal of the American Chemical Society Vol. 142; no. 13; pp. 6261 - 6267
Main Authors Dai, Wen, Geib, Steven J, Curran, Dennis P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
RADICAL DEAROMATIZATION
GENERATION
ARYLATION
LIGHT
ARENES
PHOTOREDOX CATALYSIS
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Summary:Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron-poor aromatic rings under photoredox conditions provide dearomatized 3-NHC-boryl-1,5-cycohexadienes, which are formally products of 1,4-hydroboration reactions. When regioisomers are possible, the more crowded (doubly ortho-substituted) product is formed preferably or exclusively. The mechanism may involve oxidation of the NHC-borane to an NHC-boryl radical, reduction of the electron-poor aromatic ring to a radical anion, coupling of the radical and the radical anion to give a cyclohexadienyl anion, and finally regioselective protonation.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c00490