Copper-catalysed C(sp3)–N coupling initiated by selective C–C bond cleavage of cyclobutanone oxime esters
Literature Information
Publication Date
2019-02-27
DOI
10.1039/C9QO00235A
Impact Factor
5.281
Authors
Qing-Qiang Min, Na Li, Guang-Le Chen
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
![2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol structure](https://static.chemtradehub.com/structs/416/4162-45-2-b3d6.webp "2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol structure")
2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol
CAS Number:
4162-45-2
Molecular Formula:
C19H20Br4O4
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