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2013 , Vol. 33 >Issue 12: 2460 - 2468

DOI: https://doi.org/10.6023/cjoc201307014

综述与进展

过渡金属催化烷基羧酸的脱羧偶联反应研究进展

  • 戴建军 ,
  • 王光祖 ,
  • 徐小岚 ,
  • 许华建
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  • a 合肥工业大学医学工程学院 合肥 230009;
    b 安徽医科大学基础医学院 合肥 230032;
    c 先进功能材料与器件安徽省重点实验室 合肥 230009

收稿日期: 2013-07-09

  修回日期: 2013-08-25

  网络出版日期: 2013-08-29

基金资助

国家自然科学基金(Nos. 21272050，21072040)资助项目.

收起

Recent Advances in Transition Metal Catalyzed Decarboxylative Coupling Reactions of Alkyl Carboxylic Acid

  • Dai Jianjun ,
  • Wang Guangzu ,
  • Xu Xiaolan ,
  • Xu Huajian
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  • a School of Chemical Engineering, School of Medical Engineering, Hefei University of Technology, Hefei 230009;
    b School of Medical Sciences, Anhui Medical University, Hefei 230032;
    c Key Laboratory of Advanced Functional Materials and Devices, Anhui Province, Hefei 230009

Received date: 2013-07-09

  Revised date: 2013-08-25

  Online published: 2013-08-29

Supported by

Project Supported by the National Natural Science Foundation of China (Nos. 21272050, 21072040).

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摘要

羧酸是一类廉价、易得、容易存储运输的化合物. 自芳基羧酸的脱羧Heck反应被报道以来，发展过渡金属催化的脱羧偶联反应引起了人们的广泛兴趣并已成为当前的一个研究热点. 过渡金属催化的烷基偶联反应对合成非平面的有机分子具有重要意义. 因此，发展过渡金属催化的烷基羧酸脱羧偶联反应得到了人们的广泛重视. 我们从催化脱羧偶联的过渡金属出发，分别总结了：(1)铜催化脯氨酸衍生物与炔烃(Csp3—Csp)、吲哚(Csp3—Csp2)、硝基甲烷(Csp3—Csp2)等亲核试剂的脱羧偶联反应、丙二酸单硫酯和醛的脱羧Aldol加成反应、Mannich型脱羧加成反应以及和炔溴的脱羧偶联反应；(2)钯催化吡啶-2-乙酸盐、2，2-二取代氰基乙酸、硝基取代苯乙酸等底物和卤代芳烃的脱羧偶联反应；(3)银催化烷基羧酸的脱羧氯化、氟化以及炔化反应.

关键词： 过渡金属; 脱羧偶联; 烷基羧酸; 进展

本文引用格式

戴建军 , 王光祖 , 徐小岚 , 许华建 . 过渡金属催化烷基羧酸的脱羧偶联反应研究进展[J]. 有机化学, 2013 , 33(12) : 2460 -2468 . DOI: 10.6023/cjoc201307014

Abstract

Carboxylic acids are cheap, readily available, easy to store and handle compounds. Since the studies of decarboxylative Heck reaction of aryl carboxylic acids, transition metal-catalyzed decarboxylative coupling reactions have become an interesting research area. Transition metal-catalyzed alkyl coupling plays an important role in the synthesis of nonplanar molecule. Thus, much attention has been paid to the development of transition metal-catalyzed decarboxylative cross-coupling reactions of alkyl carboxylic acids. This review focuses on: (1) the copper-catalyzed decarboxylative coupling reaction between proline derivatives and nucleophilies including terminal alkynes (Csp3—Csp), indoles (Csp3—Csp2) and nitromethane (Csp3—Csp2), the copper-catalyzed decarboxylative aldol reaction of thioester derivatives, the copper-catalyzed decarboxylative Mannich-type reaction; the copper-catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts; (2) the palladium-caytalyzed decarboxylative couplings of 2-(2-azaaryl)acetates, cyanoacetate, salts, nitrophenyl acetates salts with aryl halides; (3) the silver-catalyzed decarboxylative chlorination, fluorination and alkynylation.

Key words： transition metals; decarboxylative coupling; alkyl carboxylic acid; advance

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