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2017 , Vol. 37 >Issue 6: 1322 - 1337

DOI: https://doi.org/10.6023/cjoc201702051

综述与进展

钯催化卤代烷烃参与的自由基型转化反应

  • 周文俊 ,
  • 张逸寒 ,
  • 曹光梅 ,
  • 刘惠东 ,
  • 余达刚
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  • a. 内江师范学院化学化工学院 内江 641112;
    b. 四川大学化学学院 绿色化学与技术教育部重点实验室 成都 610064

收稿日期: 2017-02-28

  修回日期: 2017-05-05

  网络出版日期: 2017-05-17

基金资助

国家重点基础研究发展计划（973计划，No.2015CB856600）资助项目.

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Palladium-Catalyzed Radical-Type Transformations of Alkyl Halides

  • Zhou Wen-Jun ,
  • Zhang Yihan ,
  • Cao Guangmei ,
  • Liu Huidong ,
  • Yu Da-Gang
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  • a. College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang 641112;
    b. Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064

Received date: 2017-02-28

  Revised date: 2017-05-05

  Online published: 2017-05-17

Supported by

Project supported by the National Program on Key Basic Research Project of China (973 Program, No. 2015CB856600).

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摘要

钯催化的交叉偶联反应经历了数十年的发展，已经成为一种重要的有机合成手段.相比于芳基和烯基卤代物，烷基卤代物参与的偶联反应具有诸多挑战，例如烷基卤代物和钯催化剂发生氧化加成较为困难，之后形成的烷基钯物种也面临易于发生β-H消除和质子化等副反应的挑战.近年来，有机化学家们大力发展了涉及单电子转移的新型钯催化体系，实现了烷基卤代物参与的一系列自由基型偶联反应，弥补了传统双电子转化模式的不足.本文以参与反应的底物类型为序，综述了近年来钯催化卤代烷烃的自由基型转化反应新进展.

关键词： 钯催化; 卤代烷烃; 自由基

本文引用格式

周文俊 , 张逸寒 , 曹光梅 , 刘惠东 , 余达刚 . 钯催化卤代烷烃参与的自由基型转化反应[J]. 有机化学, 2017 , 37(6) : 1322 -1337 . DOI: 10.6023/cjoc201702051

Abstract

Palladium-catalyzed cross-coupling reactions have been developed for decades as useful methods in organic synthesis. Compared to aryl and alkenyl halides, alkyl halides are more challenging to be applied in cross-coupling reactions. This mainly arises from the difficulty in oxidative addition of alkyl halides to palladium catalyst, sluggish reductive elimination and competitive side reactions, such as β-H elimination and protonation, of the resulting alkylpalladium intermediates. These challenges have partly been overcome with the significant development of novel palladium catalysis involving single election transfer. A variety of cross couplings of alkyl halides have been developed. In this review the recent palladium-catalyzed radical alkylation using alkyl halides with the order of different types of coupling partners is summarized.

Key words： palladium catalysis; alkyl halide; free radical

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