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2023 , Vol. 43 >Issue 8: 2647 - 2663

DOI: https://doi.org/10.6023/cjoc202303020

综述与进展

可见光氧化还原催化炔基化反应的研究进展

  • 归春明 ,
  • 周潼瑶 ,
  • 王海峰 ,
  • 严琼姣 ,
  • 汪伟 ,
  • 黄锦 ,
  • 陈芬儿
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  • a 武汉工程大学药物研究院 武汉 430205
    b 武汉工程大学邮电与信息工程学院 武汉 430073
    c 复旦大学化学系 上海 200433

收稿日期: 2023-03-15

  修回日期: 2023-04-19

  网络出版日期: 2023-05-06

基金资助

国家自然科学基金(21602144); 湖北省教育厅科学研究计划(Q20211503)

收起

Recent Advances in Visible Light Photoredox-Catalyzed Alkynylation

  • Chunming Gui ,
  • Tongyao Zhou ,
  • Haifeng Wang ,
  • Qiongjiao Yan ,
  • Wei Wang ,
  • Jin Huang ,
  • Fener Chen
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  • a Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205
    b College of Post and Telecommunication, Wuhan Institute of Technology, Wuhan 430073
    c Department of Chemistry, Fudan University, Shanghai 200433
*;
;

Received date: 2023-03-15

  Revised date: 2023-04-19

  Online published: 2023-05-06

Supported by

The National Natural Science Foundation of China(21602144); The Scientific Research Project of Education Department of Hubei Province(Q20211503)

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摘要

炔烃的合成与转化一直是合成化学领域一个重要的研究内容, 如何在有机分子中高效快速地引入炔基官能团一直备受关注. 光氧化还原催化可利用绿色清洁的光能在较为温和的条件下产生高活性的自由基中间体, 被广泛地应用于有机合成中. 相对于传统过渡金属催化的Sonogashira反应, 光氧化还原催化炔基化反应在最近十年取得了长足发展, 且与前者形成了很好的互补之势. 该类炔基化反应既可通过端炔与铜形成的炔铜中间体进行, 又可通过非端炔的炔基自由基或炔基的自由基加成消除进行. 此外, 由于能用于该光催化炔基化反应的自由基源种类众多, 使得传统Sonogashira反应类型得到了很好补充. 根据炔基化反应成键的类型, 对近年来可见光促进的炔基化反应进行了简要总结.

关键词： 炔基化; 自由基; 光氧化还原; Sonogashira偶联

本文引用格式

归春明 , 周潼瑶 , 王海峰 , 严琼姣 , 汪伟 , 黄锦 , 陈芬儿 . 可见光氧化还原催化炔基化反应的研究进展[J]. 有机化学, 2023 , 43(8) : 2647 -2663 . DOI: 10.6023/cjoc202303020

Abstract

The synthesis and transformations of alkynes have held an important position in the field of organic synthesis. How to rapidly introduce alkynyl into organic molecules has been of great interest. Photoredox catalysis has been widely used in organic synthesis because it can generate high reactive free radical intermediates under mild conditions using green and clean energy. Visible light photocatalytic alkynylation has flourished in the last decade, which is believed to be a significant complement to the classic transition-metal-catalyzed Sonogashira reaction. This alkynylation could take place via in situ generated copper acetylide complex from terminal alkynes and copper, which also occurs through alkynyl radical species or radical addition elimination of non-terminal alkynes. Moreover, it was a good supplement to Sonogashira reaction that various radical precursors could be applied to alkynylation by visible-light photoredox catalysis. Based on the type of bonding of alkynylation, the research progress of alkynylation reactions by visible-light photoredox catalysis is reviewed, and the future development of this field is prospected.

Key words： alkynylation; radicals; photoredox; Sonogashira coupling

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