Gold-Catalyzed Highly Selective Photoredox C(sp(2) )-H Difluoroalkylation and Perfluoroalkylation of Hydrazones
| Autor: | Fei Chen, Nina Mehrkens, Frank Rominger, Tuo Zhang, A. Stephen K. Hashmi, Matthias Rudolph, Jin Xie |
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| Rok vydání: | 2015 |
| Předmět: |
010405 organic chemistry
chemistry.chemical_element General Chemistry 010402 general chemistry Highly selective 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences law.invention chemistry law Reagent Photocatalysis Fluorine Molecule Organic chemistry Electron paramagnetic resonance |
| Zdroj: | Angewandte Chemie (International ed. in English). 55(8) |
| ISSN: | 1521-3773 |
| Popis: | The first gold-catalyzed photoredox C(sp(2) )-H difluoroalkylation and perfluoroalkylation of hydrazones with readily available RF -Br reagents is reported. The resulting gem-difluoromethylated and perfluoroalkylated hydrazones are highly functionalized, versatile molecules. A mild reduction of the coupling products can efficiently produce gem-difluoromethylated β-amino phosphonic acids and β-amino acid derivatives. In mechanistic studies, a difluoroalkyl radical intermediate was detected by an EPR spin-trapping experiment, indicating that a gold-catalyzed radical pathway is operating. |
| Databáze: | OpenAIRE |
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