期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 56, 页码 13030-13036出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903242
关键词
carbenes; heterocycles; reactive intermediates; tautomerism; zwitterions
资金
- CNRS
- Agence Nationale de la Recherche [ANR-16-CE07-0006, ANR-16-CE07-0019]
- Agence Nationale de la Recherche (ANR) [ANR-16-CE07-0019, ANR-16-CE07-0006] Funding Source: Agence Nationale de la Recherche (ANR)
Coupling between 5-bromoimidazo[1,5-a]pyridinium salts and malonate or arylacetate esters leads to a facile and straightforward access to the new mesoionic, fused, tricyclic system of imidazo[2,1,5-cd]indolizinium-3-olate. Mechanistic studies show that the reaction pathway consists of nucleophilic aromatic substitution on the cationic, bicyclic heterocycle by an enolate-type moiety and in the nucleophilic attack of a transient free N-heterocyclic carbene (NHC) species on the ester group; the relative order of these two steps depends on the nature of the starting ester. This work highlights the valuable implementation of free NHC species as key intermediates in synthetic chemistry, beyond their classical use as stabilizing ligands or organocatalysts.
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