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Cu‐Catalyzed Selective Oxy‐Cyanoalkylation of Allylamines with Cycloketone Oxime Esters and CO2
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2019-11-25 , DOI: 10.1002/cjoc.201900384
Chuan‐Kun Ran 1, 2 , He Huang 2 , Xing‐Hui Li 2 , Wei Wang 2 , Jian‐Heng Ye 2 , Si‐Shun Yan 2 , Bi‐Qin Wang 1 , Chun Feng 1 , Da‐Gang Yu 2, 3
Affiliation  

The radical‐initiated carboxylative cyclization of allylamines with CO2 represents an efficient and highly promising strategy to afford valuable 2‐oxazolidinones. However, the radical precursors and pathways to generate radicals in such processes are still limited. Herein, we report the first Cu‐catalyzed selective oxy‐cyanoalkylation of allylamines with cycloketone oxime esters and CO2 via C—C bond cleavage. Many cyanoalkyl‐substituted 2‐oxazolidinones are obtained in moderate to good yields with high regio‐ and chemo‐selectivities. The utility of this redox‐neutral and cyanide‐free method is demonstrated with mild conditions, broad substrate scope, good functional group tolerance and easy scalability.

中文翻译:

铜催化的烯丙基胺与环酮肟酯和CO2的选择性氧氰基烷基化反应

烯丙基胺与CO 2的自由基引发的羧基环化反应是一种有效且很有前途的策略,可提供有价值的2-恶唑烷酮。但是,自由基前体和在这种方法中产生自由基的途径仍然受到限制。在此,我们报道了通过CC键断裂,用环酮肟酯和CO 2 进行的烯丙基胺的第一个铜催化的选择性氧氰基烷基化反应。以中等到良好的产率获得了许多氰基烷基取代的2-恶唑烷酮,具有很高的区域选择性和化学选择性。在温和的条件下,广泛的底物范围内,良好的官能团耐受性和易于扩展性上证明了这种无氧化还原中性和无氰化物方法的实用性。
更新日期:2019-11-26
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