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化学进展 2018, Vol. 30 Issue (8): 1082-1096 DOI: 10.7536/PC171246 前一篇   后一篇

• 综述 •

功能化烯胺的合成

袁梦娅, 陈孝云*, 林生岭*   

  1. 江苏科技大学环境与化学工程学院 镇江 212003
  • 收稿日期:2017-12-29 修回日期:2018-03-28 出版日期:2018-08-15 发布日期:2018-05-16
  • 通讯作者: 陈孝云, 林生岭 E-mail:xiaoyun_chen12@163.com;linshl5757@sina.com
  • 基金资助:
    国家自然科学基金项目（No.21602085）和江苏省基础研究计划（自然科学基金）项目（No.BK20160551）资助
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Synthesis of the Functionalized Enamine

Mengya Yuan, Xiaoyun Chen*, Shengling Lin*   

  1. School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China
  • Received:2017-12-29 Revised:2018-03-28 Online:2018-08-15 Published:2018-05-16
  • Supported by:
    The work was supported by the National Natural Science Foundation of China(No.21602085) and the Natural Science Foundation of Jiangsu Province(No.BK20160551).
烯胺作为许多药物的关键结构单元，在有机合成，特别是天然产物的合成和含氮杂环化合物的合成中有很重要的应用。为了更好地发展适用性广的合成新方法，本文综述合成烯胺的最新研究进展。首先总结了传统合成烯胺的相关工作，随后综述了催化合成烯胺的相关工作，包括烯烃的催化胺化和炔烃氢胺化反应，详细介绍了过渡金属（主要是Cu（Ⅰ或Ⅱ）或Pd（0或Ⅱ））催化的Buchwald-Harwig反应中，使用多种取代烯烃（包括卤代烯烃及拟卤代烯烃与烯基硼酸）作为底物的研究进展，同时，对通过C（sp2）—H直接活化来构筑与不同胺相连的C—N键的Aza-Wacker氧化偶合反应也进行了介绍。希望对发展合成烯胺的新方法有所裨益。
关键词： 烯胺, 烯烃, 取代烯烃, 炔烃, 胺试剂
Enamines, with one amino group connected with carbon-carbon double bond, are key frameworks of many drugs. They have important applications in organic synthesis, especially in the synthesis of natural products and N-containing heterocycles owing to their unique structures. Therefore, the synthesis of enamines is particularly noticeable. In order to develop novel and applicable methodologies to synthesize enamines, the recent progress in their synthesis has been reviewed herein. Firstly, the related work of conventional synthesis, which include condensation reaction, addition reaction, heterocyclic cracking Curtius rearrangement, Wittig reaction, α, β-elimination of amide, reductive acylation of ketoxime, etc. has been summarized. Then, the catalytic amination of olefins to prepare enamine has been introduced in detail. In transition-metal catalyzed (mainly Cu (Ⅰ or Ⅱ) or Pd (0 or Ⅱ)) Buchwald-Hartwig reaction, the research progress of using various substituted olefins as substrates, including halogenated olefins, pseudohalogenated olefins and alkenyl boronic acid, has been reviewed. The methodology called Aza-Wacker oxidative coupling reaction to synthesize enamine via C (sp2)-H direct activation to construct C-N bond with different amines have also been summarized. Finally, the progress to prepare enamines and their derivatives by hydroamination of alkynes has been introduced here. It is of great significance for the development of the new methodologies to synthesize enamine.
Contents
1 Introduction
2 Synthese of enamine by traditional methods
3 Synthese of enamine from olefins and amines
3.1 Synthese of enamine from substituted olefins and amines
3.2 Synthese of enamine by C-H activation of olefins
4 Synthese of enamine from alkynes and amines
4.1 Synthese of enamine from alkynes and aliphatic amines and its derivatives
4.2 Synthese of enamine from alkynes and aromatic amines
4.3 Synthese of enamine from alkynes and amides and its derivatives
4.4 Synthese of enamine from alkynes and diazo or azide
5 Conclusion
Key words: enamine, olefins, substituted olefins, alkynes, amine reagents

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摘要

功能化烯胺的合成