| Autor: |
Dai W; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15208, United States., Geib SJ; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15208, United States., Curran DP; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15208, United States. |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of the American Chemical Society [J Am Chem Soc] 2020 Apr 01; Vol. 142 (13), pp. 6261-6267. Date of Electronic Publication: 2020 Mar 23. |
| DOI: |
10.1021/jacs.0c00490 |
| Abstrakt: |
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. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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