期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 27, 页码 8310-8315出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801676
关键词
Breslow intermediates; carbenes; NMR spectroscopy; reaction mechanisms; umpolung
资金
- Deutsche Forschungsgemeinschaft [1087, BE 998/14-1]
- Fonds der Chemischen Industrie
- BASF SE
We report the first generation and characterization of elusive Breslow intermediates derived from aromatic N-heterocyclic carbenes (NHCs), namely benzimidazolin-2-ylidenes (NMR, X-ray analysis) and thiazolin-2-ylidenes (NMR). In the former case, the diamino enols were generated by reaction of the free N,N-bis(2,6-diisopropylphenyl)- and N,N-bis(mesityl)-substituted benzimidazolin-2-ylidenes with aldehydes while the dimer of 3,4,5-trimethylthiazolin-2-ylidene served as the starting material in the latter case. The unambiguous NMR identification of the first thiazolin-2-ylidene-based Breslow intermediate rests on double C-13 labeling of both the NHC and the aldehyde component. The acyl anion reactivity was confirmed by benzoin formation with excess aldehyde.
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