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2023 , Vol. 43 >Issue 9: 3098 - 3106

DOI: https://doi.org/10.6023/cjoc202303016

综述与进展

氯仿参与的烯烃自由基加成反应的研究进展

  • 张建涛 ,
  • 张聪 ,
  • 莫诺琳 ,
  • 罗佳婷 ,
  • 陈莲芬 ,
  • 刘卫兵
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  • a 广东石油化工学院化学学院 广东茂名 525000
    b 肇庆学院环境与化学工程学院 广东肇庆 526061

收稿日期: 2023-03-11

  修回日期: 2023-04-17

  网络出版日期: 2023-05-11

基金资助

广东石油化工学院人才引进计划(2019rc048); 茂名市科技计划(2022031); 国家自然科学基金(22002139); 广东省基础与应用基础研究基金(2019A1515110550)

收起

Research Progress in Radical Addition Reaction of Alkenes Involving Chloroform

  • Jiantao Zhang ,
  • Cong Zhang ,
  • Nuolin Mo ,
  • Jiating Luo ,
  • Lianfen Chen ,
  • Weibing Liu
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  • a College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000
    b School of Environmental and Chemical Engineering, Zhaoqing University, Zhaoqing, Guangdong 526061
* E-mail: ;
;

Received date: 2023-03-11

  Revised date: 2023-04-17

  Online published: 2023-05-11

Supported by

Projects of Talents Recruitment of Guangdong University of Petrochemical Technology(2019rc048); Science and Technology Planning Project of Maoming City(2022031); National Natural Science Foundation of China(22002139); Guangdong Basic and Applied Basic Research Foundation(2019A1515110550)

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摘要

多卤甲基化合物, 尤其是具有二氯甲基或三氯甲基结构的多氯甲基化合物, 被广泛应用于医药、农业及有机功能材料等领域. 此外, 多氯甲基还可以很容易地转化为氨基、羟基、羧基和羰基等各种官能团, 这些官能团可进一步用于构建复杂的环状结构. 因此, 开发有效的多氯甲基化策略, 在许多具有生物活性的天然分子的合成中具有重要的意义. 氯仿是一种容易获得的化学资源, 在自由基引发剂存在下可发生自由基转化, 通过氢原子转移(HAT)形成•CCl3自由基或通过卤素原子转移(XAT)形成•CHCl2自由基. 按照氯仿产生自由基种类的不同, 对氯仿参与烯烃自由基加成, 从而构建多氯甲基取代化合物的最新研究进展进行了梳理和总结, 并对反应范围、局限性以及部分机理进行了讨论.

关键词： 多卤甲基化合物; 多氯甲基化; 氯仿; 烯烃; 自由基加成

本文引用格式

张建涛 , 张聪 , 莫诺琳 , 罗佳婷 , 陈莲芬 , 刘卫兵 . 氯仿参与的烯烃自由基加成反应的研究进展[J]. 有机化学, 2023 , 43(9) : 3098 -3106 . DOI: 10.6023/cjoc202303016

Abstract

Polyhalomethyl compounds, especially those with dichloromethyl or trichloromethyl structures, are widely used in fields, such as medicine, agriculture and organic functional materials. In addition, polychloromethyl could also be easily converted into various functional groups, such as amino, hydroxyl, carboxyl and carbonyl groups, which could be further used to construct complex ring structures. Therefore, the development of effective polychlorinated methylation strategies has important research significance in the synthesis of many natural molecules with biological activities. Chloroform is an easily available chemical resource that can undergo free radical transformation in the presence of free radical initiators, forming •CCl3 radical through hydrogen atom transfer (HAT) and •CHCl2 radical through halogen atom transfer (XAT). According to the different types of free radicals produced by chloroform, the latest research progress of chloroform participating radical addition of alkenes to construct polychloromethyl substituted compounds is summarized, and the reaction range, limitations and some mechanisms are also discussed.

Key words： polyhalomethyl compound; polychlorinated methylation; chloroform; alkene; radical addition

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