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2014 , Vol. 34 >Issue 12: 2385 - 2405

DOI: https://doi.org/10.6023/cjoc201406049

综述与进展

叔膦促进下两种亲电试剂之间的环化反应研究进展

  • 周荣 ,
  • 刘蓉芳 ,
  • 李瑞丰 ,
  • 贺峥杰
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  • a. 太原理工大学化学化工学院 太原 030024;
    b. 南开大学元素有机化学国家重点实验室 天津化学化工协同创新中心 天津 300071

收稿日期: 2014-06-29

  修回日期: 2014-08-12

  网络出版日期: 2014-08-28

基金资助

国家自然科学基金(No.21272119)、太原理工大学引进人才基金(No.tyutrc-201357a)及太原理工大学青年基金(No.2013Z043)资助项目.

收起

Progress in Phosphine-Promoted Annulations between Two Electrophiles

  • Zhou Rong ,
  • Liu Rongfang ,
  • Li Ruifeng ,
  • He Zhengjie
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  • a. College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024;
    b. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071

Received date: 2014-06-29

  Revised date: 2014-08-12

  Online published: 2014-08-28

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272119), the Qualified Personnel Foundation of Taiyuan University of Technology (No. tyutrc-201357a), and the Youth Foundation of Taiyuan University of Technology (No. 2013Z043).

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摘要

发展环状化合物的高效合成方法对药物分子、天然产物及其他功能有机分子的合成具有重要意义. 近年来, 叔膦促进下两种亲电试剂之间的环化反应, 由于具有原料简单易得、反应条件温和、且无需金属参与等优点, 同时为多种碳环及杂环化合物的合成提供了高效的新途径, 因而受到了合成化学家的广泛关注. 这类反应通常经过叔膦对亲电试剂进行亲核加成, 产生两性离子活性中间体这一关键步骤来完成. 根据两性离子的不同来源, 综述了叔膦促进下缺电子联烯、Morita-Baylis-Hillman烯丙基化合物、缺电子烯烃与其他亲电试剂之间的环化反应.

关键词： 叔膦; 亲电试剂; 两性离子; 环化反应

本文引用格式

周荣 , 刘蓉芳 , 李瑞丰 , 贺峥杰 . 叔膦促进下两种亲电试剂之间的环化反应研究进展[J]. 有机化学, 2014 , 34(12) : 2385 -2405 . DOI: 10.6023/cjoc201406049

Abstract

The development of highly efficient synthetic methods of cyclic compounds is of great significance in the syntheses of pharmaceutically active molecules, natural products and other functional organic molecules. Recently, phosphine-promoted annulations of two electrophiles, which provide highly efficient access to various carbo-and heterocycles, have attracted extensive interest from synthetic chemists due to their merits such as ready availability of starting materials, mild and metal-free conditions. Generally, this kind of annulation reaction proceeds through a key step to generate an active zwitterionic intermediate via nucleophilic addition of the phosphine to an electrophile. According to different sources of the zwitterions, this review summarizes the recent progress in phosphine-promoted annulations of electron-deficient allenes, Morita-Baylis-Hillman allylic adducts, and electron-deficient alkenes with other electrophiles.

Key words： phosphine; electrophile; zwitterions; annulations

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