Ru(II)-Catalyzed Cross-Coupling of Cyclopropenes with Diazo Compounds: Formation of Olefins from Two Different Carbene Precursors
| Autor: | Hang Zhang, Jianbo Wang, Yan Zhang, Heng Yi, Bo Wang, Tong Sun |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Double bond 010405 organic chemistry Carbene dimerization Organic Chemistry Cyclopropene 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Nucleophile Stereoselectivity Diazo Carbene |
| Zdroj: | The Journal of Organic Chemistry. 83:1026-1032 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.7b02634 |
| Popis: | Formal carbene dimerization is a convergent method for the synthesis of alkenes. Herein, we report a Ru(II)-catalyzed carbene dimerization of cyclopropenes and diazo compounds. The yields are up to 97% and the stereoselectivity are up to >20:1. Mechanistically, it has been experimentally demonstrated that the catalyst reacts with cyclopropene first to generate a Ru(II)–carbene species, which is attacked by nucleophilic diazo substrate, followed by dinitrogen extrusion to form the double bond. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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