Copper-catalysed C(sp3)–N coupling initiated by selective C–C bond cleavage of cyclobutanone oxime esters
| Autor: | Feng Liu, Na Li, Qing-Qiang Min, Guang-Le Chen |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Organic Chemistry chemistry.chemical_element Cyclobutanone 010402 general chemistry Oxime 01 natural sciences Medicinal chemistry Copper 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Amine gas treating Bond cleavage Amination Alkyl |
| Zdroj: | Organic Chemistry Frontiers. 6:1200-1204 |
| ISSN: | 2052-4129 |
| DOI: | 10.1039/c9qo00235a |
| Popis: | Here we report an efficient copper-catalysed selective C–C bond cleavage/amination of cyclobutanone oxime esters. This reaction protocol is operationally simple and conducted at ambient temperature, allowing access to a wide range of functionalized 4-(arylamino)butanenitriles in moderate to excellent yields. This transformation shows high chemo-selectivity and wide functional-group compatibility and can be easily scaled up to the gram level with a useful yield. A mechanism involving copper-catalysed capture of alkyl radical intermediates by amine nucleophiles is proposed. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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