Recent Advances in Visible Light Induced Radical 1,2-Functionalization of Alkynes

doi:10.6023/A24030090

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可见光介导炔烃的自由基1,2-官能团化反应新进展

李康葵^a, 龙先扬^a, 黄岳^a, 祝诗发^a,b,*

^a华南理工大学化学与化工学院广东省功能分子工程重点实验室广州 510640;
^b浙江理工大学化学与化工学院杭州 310018

投稿日期:2024-03-18
作者简介:李康葵,男,汉族,1992年出生于湖南耒阳; 2015年6月本科毕业于怀化学院,2017年9考入云南民族大学有机化学专业攻读硕士学位,导师为樊保敏教授,于2020年6月毕业并获得理学硕士学位; 同年9月考入华南理工大学攻读博士学位,在导师祝诗发教授的指导下开展学位论文研究工作,研究方向为乙炔的高值转化; 龙先扬,男,壮族,2000年出生于广西南宁; 2022年6月本科毕业于广西大学,同年9月考入华南理工大学,并加入祝诗发教授课题组攻读硕士学位,研究方向为乙炔的官能团化反应; 黄岳,男,壮族,2001年出生于广西百色; 2023年6月本科毕业于广西大学,同年9月考入华南理工大学,并加入祝诗发教授课题组攻读硕士学位,研究方向为乙炔的官能团化反应; 祝诗发,华南理工大学二级教授、博导; 2001年6月本科毕业于湖南大学,同年考入中科院上海有机所硕博连读,导师为朱仕正研究员,2006年6月获中科院上海有机所理学博士学位; 同年9月赴美,先后在Syracuse University和University of South Florida 从事博士后研究; 2009年5月,作为“海外优秀引进人才”入职华南理工大学化学与化工学院; 国家自然科学基金-优秀青年基金获得者,先后入选“教育部新世纪优秀人才支持计划”、“科技部中青年科技创新领军人才和国家“万人计划”科技创新领军人才,担任Green Synth. Catal.和《有机化学》杂志编委; 研究方向为炔烃的多样性精准转化
基金资助:
国家自然科学基金（Nos. 22071062,22271096）和中央高校基本科研业务费专项资金（No. 2022ZYGXZR107）资助

Recent Advances in Visible Light Induced Radical 1,2-Functionalization of Alkynes

Li Kangkui^a, Long Xianyang^a, Huang Yue^a, Zhu Shifa^a,b,*

^aKey Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
^bSchool of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018

Received:2024-03-18
Contact: * E-mail: zhusf@scut.edu.cn
Supported by:
National Natural Science Foundation of China (Nos. 22071062 and 22271096) and the Fundamental Research Funds for the Central Universities, SCUT (2022ZYGXZR107).

As one of the most basic functional groups in organic molecules, the carbon-carbon triple bond containing two π-bonds harbor great potential for diverse organic transformations. Among them, the functionalization reaction based on the addition of free radicals to alkynes is an effective way to synthesize diverse functionalized olefins, ketones, and even alkane molecules, as well as an important tool for constructing multiple chemical bonds simultaneously. In the last decade, the application of visible light-induced radical reaction strategy for alkyne functionalization has received widespread attention due to it align with the concepts of green chemistry and sustainable development. Nowadays, photoinduced radical functionalization of alkynes has been developed unprecedentically, and many new methods have emerged. Indeed, light-induced radical functionalization reactions of alkynes provide a relatively green approach to the diverse transformations of alkynes. These conversions include hydrofunctionalization, oxidative functionalization, difunctionalization, and so on. These reactions feature mild conditions and easy operation, and do not even require the addition of metals and photosensitizers. Importantly, they provide an efficient way for the construction of valuable skeletons. In particular, the difunctionalization reaction enables the synthesis of high-added-value challenging molecules from simple feedstocks. In these reactions, the alkenyl radicals formed by radical addition to alkynes are the key intermediates. Thus, the type of radical precursor and the further transformation of the alkenyl radical determine the type of chemical bond constructed and the structure of the final product. This paper mainly reviews the new advances in photoinduced radical 1,2-functionalization reactions of alkynes in the past five years, classifying them in terms of the types of chemical bonds constructed, and providing a systematic summary of the types of radicals and reactions. The mechanism and universality of the reactions, as well as its advantages and disadvantages were discussed, and the challenges and opportunities facing the field were outlooked as well.

Key words: visible light, alkynes, radical reaction, functionalization, photocatalysis

Cite this article

Li Kangkui, Long Xianyang, Huang Yue, Zhu Shifa. Recent Advances in Visible Light Induced Radical 1,2-Functionalization of Alkynes[J]. Acta Chimica Sinica, doi: 10.6023/A24030090.

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可见光介导炔烃的自由基1,2-官能团化反应新进展

Recent Advances in Visible Light Induced Radical 1,2-Functionalization of Alkynes

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