可见光介导炔烃的自由基1,2-官能团化反应新进展

doi:10.6023/A24030090

化学学报 ›› 2024, Vol. 82 ›› Issue (6): 658-676.DOI: 10.6023/A24030090 上一篇下一篇

综述

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 发布日期:2024-04-28

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月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:
项目受国家自然科学基金(22071062); 项目受国家自然科学基金(22271096); 中央高校基本科研业务费专项资金(2022ZYGXZR107)

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

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

a Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640
b School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018

Received:2024-03-18 Published:2024-04-28
Contact: * E-mail: zhusf@scut.edu.cn
Supported by:
National Natural Science Foundation of China(22071062); National Natural Science Foundation of China(22271096); Fundamental Research Funds for the Central Universities, SCUT(2022ZYGXZR107)

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摘要/Abstract

作为有机分子中最基本的官能团之一, 包含两个π键的碳碳三键蕴藏着多样有机转化的巨大潜力. 其中, 基于自由基对炔烃加成的官能团化反应是合成多样的功能化烯烃、酮, 乃至烷烃分子的有效途径, 同时也是构建多个化学键的重要手段. 近十几年来, 由于可见光介导的自由基反应策略符合绿色化学和可持续发展的理念, 使得这种策略在炔烃官能团化方面的应用受到了广泛的关注. 时至今日, 光介导炔烃的自由基官能团化反应得到了空前的发展, 随之涌现出许多新方法. 本文主要综述了近五年来可见光介导炔烃的自由基1,2-官能团化反应的新进展, 以构建的化学键种类进行分类, 对涉及的自由基种类和反应类型进行了系统总结. 分析讨论了反应的机理、普适性以及优势与不足, 并对该领域所面临的挑战和机遇进行了展望.

关键词: 可见光, 炔烃, 自由基反应, 官能团化, 光催化

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

引用此文

李康葵, 龙先扬, 黄岳, 祝诗发. 可见光介导炔烃的自由基1,2-官能团化反应新进展[J]. 化学学报, 2024, 82(6): 658-676.

Kangkui Li, Xianyang Long, Yue Huang, Shifa Zhu. Recent Advances in Visible Light Induced Radical 1,2-Functionalization of Alkynes[J]. Acta Chimica Sinica, 2024, 82(6): 658-676.

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图/表 55

图1. 光介导炔烃的自由基官能团化

Figure 1. Photoinduced radical functionalization of alkynes

图2. 炔烃的自由基氢官能团化反应的一般过程

Figure 2. General process of radical hydrofunctionalization of alkynes

图3. 光催化炔烃的氢三氟甲基化反应

Figure 3. Photocatalyzed hydrotrifluoromethylation of alkynes

图4. 光/高价碘试剂介导的炔烃氢二氟甲基化反应

Figure 4. Light/high-valent iodine-induced hydrodifluoromethylation of alkynes

图5. 光介导炔烃的二氟烷基化反应

Figure 5. Photoinduced difluoroalkylation of alkynes

图6. 光/镍协同催化炔烃的氢烷基化反应

Figure 6. Photoredox/nickel dual catalyzed hydroalkylation of alkynes

图7. 光促进铜催化端炔的氢烷基化反应

Figure 7. Photoinduced/copper-catalyzed hydroalkylation of terminal alkynes

图8. 光催化端炔的氢烷基化反应

Figure 8. Photocatalyzed hydroalkylation of terminal alkynes

图9. 光/镍协同催化炔烃的氢烷基化反应

Figure 9. Photoredox/nickel dual catalyzed hydroalkylation of alkynes

图10. 光催化端炔的氢芳基化反应

Figure 10. Photocatalyzed hydroarylation of terminal alkynes

图11. 光催化炔烃的顺式氢膦化反应

Figure 11. Photocatalyzed cis-hydrophosphination of alkynes

图12. 光介导炔烃氢膦化反应

Figure 12. Photoinduced hydrophosphylation of alkynes

图13. 光催化炔烃氢膦化反应

Figure 13. Photocatalyzed hydrophosphination reaction of alkynes

图14. 光催化炔烃与硫酚(硫醇)的反应

Figure 14. Photocatalytic reaction of alkynes with thiophenols or mercaptans

图15. 炔烃多样硫醚化反应

Figure 15. Diverse thioetherification reactions of alkynes

图16. 光催化炔烃的氢磺酰化反应

Figure 16. Photocatalyzed hydrogen-sulfonylation of alkynes

图17. 光/铜协同催化的炔烃氢硼化反应

Figure 17. Photoredox/copper dual catalyzed alkyne hydroboronation reaction

图18. 光催化炔烃的三组分氢硫化反应

Figure 18. Photocatalyzed three-component hydrosulfurization of alkynes

图19. 光/镍协同催化的炔烃官能团化反应

Figure 19. Photoredox/nickel dual catalyzed functionalization of alkyne

图20. 炔烃的自由基氧化-官能团化反应一般历程

Figure 20. General pathway of radical oxidation-functionalization of alkynes

图21. 光催化炔烃的多组分氧化-三氟甲基化反应

Figure 21. Photocatalyzed multicomponent oxidative trifluoromethylation of alkynes

图22. 可见光介导炔烃和芳基偶氮砜的反应

Figure 22. Visible-light-induced reaction of alkyne and arylazo sulfone

图23. 炔烃的氧化-硫氰化反应

Figure 23. Oxidation-thiocyanation reaction of alkynes

图24. 炔烃的氧化-磺酰化反应

Figure 24. Oxidation-sulfonylation of alkynes

图25. 光介导炔烃膦酰化-氧化反应

Figure 25. Photoinduced phosphonylation-oxidation of alkynes

图26. 炔烃的自由基双官能团化反应的一般过程

Figure 26. General process of radical bifunctional process of alkynes

图27. 光/镍协同催化炔烃的自由基三组分交叉偶联反应的一般历程

Figure 27. General pathway of photoredox/nickel dual catalyzed three-component cross-coupling reaction of alkyne

图28. 光/镍协同催化炔烃顺式芳基烷基化反应

Figure 28. Photoredox/nickel dual catalyzed Z-aryl-alkylation of alkynes

图29. 光/镍协同催化炔烃的烷基芳基化反应

Figure 29. Photoredox/nickel dual catalyzed alkyl-arylation of alkynes

图30. 光/镍协同催化的端炔的烷基-烯丙基化反应

Figure 30. Photoredox/nickel dual catalyzed allyl-alkylation of terminal alkynes

图31. 光催化的酮酸和炔烃反应

Figure 31. Photocatalyzed reaction of keto acids and alkynes

图32. 光催化乙炔双碳官能团化反应

Figure 32. Photocatalyzed double-carbon functionalization of acetylene

图33. 光催化炔烃双氰基化反应

Figure 33. Photocatalyzed bis-cyanation of alkynes

图34. 光催化炔烃的双碳官能团化反应

Figure 34. Photocatalyzed two-carbon functionalization of alkynes

图35. 光催化炔烃三氟甲基-卤化反应

Figure 35. Photocatalyzed trifluoromethyl-halogenation of alkynes

图36. 光介导炔烃的磺酰化-三氟甲基化反应

Figure 36. Photoinduced sulfonylation-trifluoromethylation of alkynes

图37. 光介导炔烃氰甲基-碘化反应

Figure 37. Photoinduced cyanomethyl-iodination of alkynes

图38. 光介导炔烃的全氟烷基-碘化反应

Figure 38. Photoinduced perfluoroalkyl-iodination of alkynes

图39. 光介导二氧化碳参与的炔烃双官能团化反应

Figure 39. Photoinduced CO2-involved difunctionalization of alkynes

图40. 季膦盐与炔烃的自由基环加成反应

Figure 40. Radical cycloaddition of quaternary phosphines with alkynes

图41. 光/镍协同催化炔烃的芳基-磺酰基化反应

Figure 41. Photoredox/nickel dual catalyzed aryl-sulfonylation of alkynes

图42. 光/镍协同催化炔烃的烯基-磺酰基化反应

Figure 42. Photoredox/Ni dual catalyzed alkenyl-sulfonylation of alkynes

图43. 光/镍协同催化炔烃的芳溴化反应

Figure 43. Photoredox/nickel dual catalyzed aryl-bromination of alkynes

图44. 光催化乙炔的双膦酰基化和膦酰化-烷基化反应

Figure 44. Photocatalyzed bisphosphonylation and phosphonylation-alkylation of acetylene

图45. 光催化乙炔双氢硫化反应

Figure 45. Photocatalyzed dihydrosulfurization of acetylene

图46. 乙炔的磺酰基-硫醚化双官能团化反应

Figure 46. Sulfonyl-thioetherylation of acetylene

图47. 光催化乙炔磺酰化-溴化反应

Figure 47. Photocatalyzed sulfonylation-bromination of acetylene

图48. 光催化炔烃磺酰基-氯化反应

Figure 48. Photocatalyzed alkyne sulfonyl-chlorination reaction

图49. 光/金协同催化炔烃硫化砜化反应

Figure 49. Light/gold dual catalyzed sulfonation of alkynes

图50. 光催化炔烃串联自由基双官能团化反应

Figure 50. Photocatalyzed radical cascade difunctionalization of alkynes

图51. 光催化炔烃氟磺酰-氯化反应

Figure 51. Photocatalyzed alkyne fluorosulfonyl-chlorination

图52. 光催化炔烃磺酰化-碘化反应

Figure 52. Photocatalyzed sulfonylation-iodination of alkynes

图53. 光促进的炔烃磺酰基化-碘化反应

Figure 53. Light-promoted sulfonylation-iodination of alkynes

图54. 光催化炔烃磺酰基-二硫醚化反应

Figure 54. Photocatalyzed sulfonyl-disulfide etheration of alkynes

图55. 光催化炔烃磺酰基-硫醚化反应

Figure 55. Photocatalyzed sulfonyl-thioetherification of alkynes

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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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