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 in | Journal of the American Chemical Society Vol. 142; no. 13; pp. 6261 - 6267 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
01.04.2020
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Dai, Wen Curran, Dennis P Geib, Steven J |
| AuthorAffiliation | Department of Chemistry |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32101418$$D View this record in MEDLINE/PubMed |
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| Snippet | Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron-poor aromatic rings under photoredox conditions provide dearomatized... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | 1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N‑Heterocyclic Carbene Boranes |
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