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Recent advances in oxidative C–C coupling reaction of amides with carbon nucleophiles
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2017-11-02 , DOI: 10.1016/j.tetlet.2017.10.081
Katsuhiko Moriyama

The C–C coupling reaction of N-electron withdrawing group (EWG) protected amides with coupling partners is one of the most important methods for C–C bond formation at the α-position of amides to directly give α-substituted amides. Of the four reactions, namely, the reaction via the generation of carbanion with an electrophile, that via the generation of carbon radical with a radical donor, that via the generation of iminium ion species with a nucleophile (oxidative coupling reaction), and that using a transition metal carbenoid, the oxidative coupling reaction presents a challenge although the reaction products are very useful for the transformation of a wide range of nitrogen-containing derivatives. In this review, recent developments in the oxidative coupling reaction of N-EWG protected amides with nucleophiles are summarized with focus on the reaction using a transition metal, the transition-metal-free reaction, the enantioselective reaction using a chiral catalysts, and the organocatalyzed oxidative coupling reaction.



中文翻译:

酰胺与碳亲核试剂的氧化CC偶联反应的最新进展

N-电子吸收基团(EWG)保护的酰胺与偶联伙伴的C–C偶联反应是在酰胺的α-位直接形成α-取代的酰胺的C–C键形成的最重要方法之一。在这四个反应中,分别是通过与亲电试剂产生碳负离子,通过自由基给体产生碳自由基,通过与亲核试剂产生亚胺离子物种的反应(氧化偶联反应)以及作为过渡金属类化合物,尽管反应产物对于转化各种含氮衍生物非常有用,但氧化偶联反应仍然是一个挑战。在这篇综述中,N的氧化偶联反应的最新进展总结了具有亲核试剂的-EWG保护的酰胺,重点关注使用过渡金属的反应,无过渡金属的反应,使用手性催化剂的对映选择性反应以及有机催化的氧化偶联反应。

更新日期:2017-11-02
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