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Copper-Catalyzed Decarboxylative Functionalization of Conjugated β,γ-Unsaturated Carboxylic Acids
ACS Catalysis ( IF 12.9 ) Pub Date : 2020-10-29 , DOI: 10.1021/acscatal.0c03621
Wei Zhang 1 , Chengming Wang 1 , Qiu Wang 1
Affiliation  

Copper-catalyzed decarboxylative coupling reactions of conjugated β,γ-unsaturated carboxylic acids have been achieved for allylic amination, alkylation, sulfonylation, and phosphinoylation. This approach was effective for a broad scope of amino, alkyl, sulfonyl, and phosphinoyl radical precursors as well as various conjugated β,γ-unsaturated carboxylic acids. These reactions also feature high regioselectivity, good functional group tolerance, and simple operation procedure. Mechanistic studies show that the reaction proceeds via copper-catalyzed electrophilic addition onto an olefin followed by decarboxylation, with radical intermediates involved. These insights present a modular and powerful strategy to access versatilely functionalized allyl-containing skeletons from readily available and stable carboxylic acids.

中文翻译:

共轭β,γ-不饱和羧酸的铜催化脱羧官能化

铜催化的共轭 β,γ-不饱和羧酸的脱羧偶联反应已用于烯丙基胺化、烷基化、磺酰化和膦酰化。这种方法对广泛的氨基、烷基、磺酰基和膦酰基自由基前体以及各种共轭 β,γ-不饱和羧酸有效。这些反应还具有区域选择性高、官能团耐受性好、操作简单等特点。机理研究表明,该反应通过铜催化亲电加成到烯烃上,然后脱羧而进行,其中涉及自由基中间体。这些见解提出了一种模块化和强大的策略,可以从容易获得且稳定的羧酸中获取多功能功能化的含烯丙基骨架。
更新日期:2020-11-21
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