Addition of N-Heterocyclic Carbenes to Imines: Phenoxide Assisted Deprotonation of an Imidazolium Moiety and Generation of Breslow Intermediates Derived from Imines
| Autor: | Hasan Koyuncu, Jean-Cédric Frison, Adrian C. Whitwood, Richard E. Douthwaite, Stevan Simonovic |
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| Rok vydání: | 2008 |
| Předmět: |
Models
Molecular chemistry.chemical_classification Molecular Structure Base (chemistry) Chemistry education Organic Chemistry Imidazoles Oxides Stereoisomerism Bond formation Crystallography X-Ray Photochemistry Biochemistry Medicinal chemistry chemistry.chemical_compound Deprotonation Heterocyclic Compounds Intramolecular force Moiety Imines Protons Physical and Theoretical Chemistry Methane Carbene |
| Zdroj: | Organic Letters. 11:245-247 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol802572n |
| Popis: | Reactions between imidazolium-imine salts and base result in C-C bond formation via intermediate N-heterocyclic carbenes. In the presence of a proximal OH moiety, carbene formation occurs via intramolecular deprotonation by phenoxide. For simple imines, a reactive Breslow-type intermediate gives access to new heterocycles with the formation of six- and seven-member rings. |
| Databáze: | OpenAIRE |
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