Recent advances in oxidative C-C coupling reaction of amides with carbon nucleophiles
Recent advances in oxidative C-C coupling reaction of amides with carbon nucleophiles
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DOI：
10.1016/j.tetlet.2017.10.081
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发表时间：
2017-12-13
影响因子：
1.8
通讯作者：
Moriyama, Katsuhiko
中科院分区：
文献类型：
--
作者：
Moriyama, Katsuhiko
N-吸电子基团（EWG）保护的酰胺与偶联物的C-C偶联反应是在酰胺的α-位形成C-C键直接得到α-取代酰胺的重要方法之一。在四种反应中，即通过与亲电试剂生成碳负离子的反应，通过与自由基供体生成碳自由基的反应，通过与亲核试剂生成亚胺离子物种的反应，（氧化偶联反应），以及使用过渡金属类卡宾，氧化偶联反应提出了一个挑战，尽管反应产物对于各种氮的转化非常有用，含有衍生物。本文综述了N-EWG保护酰胺与亲核试剂的氧化偶联反应的最新研究进展，重点介绍了过渡金属氧化偶联反应、无过渡金属氧化偶联反应、手性催化的对映选择性反应以及有机催化的氧化偶联反应。(C)2017爱思唯尔有限公司版权所有
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 a-position of amides to directly give a-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. (C) 2017 Elsevier Ltd. All rights reserved.