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Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-03-22 , DOI: 10.1002/anie.201800829
Patrick J. Moon 1 , Anis Fahandej-Sadi 1 , Wenyu Qian 1 , Rylan J. Lundgren 1
Affiliation  

The copper‐catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron‐deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.

中文翻译:

芳基和烯基硼酸酯的脱羧苯甲酸酯化

据报道,铜和芳基酯和烯基硼酸酯的铜催化脱羧苄基化反应具有电子不足的乙酸芳基酯。氧化偶合在温和的好氧条件下进行,并能耐受许多潜在的反应性亲电官能团,这对传统的苄基化方法(芳基碘化物和溴化物,质子杂原子,醛,迈克尔受体)会产生问题。机理研究支持了通过乙酸芳基酯的脱羧反应生成苄基亲核体并进而被催化剂截留而形成二芳基甲烷产物的反应途径。
更新日期:2018-03-22
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