Copper-catalysed C(sp3)–N coupling initiated by selective C–C bond cleavage of cyclobutanone oxime esters

文献情報

出版日 2019-02-27

DOI 10.1039/C9QO00235A

インパクトファクター 5.281

著者

Qing-Qiang Min, Na Li, Guang-Le Chen

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Copper-catalysed C(sp3)–N coupling initiated by selective C–C bond cleavage of cyclobutanone oxime esters

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