芳基偶氮砜的芳基化及砜基化研究进展

doi:10.6023/cjoc202107022

有机化学 ›› 2021, Vol. 41 ›› Issue (12): 4639-4650.DOI: 10.6023/cjoc202107022 上一篇下一篇

所属专题：绿色合成化学专辑；热点论文虚拟合集

综述与进展

芳基偶氮砜的芳基化及砜基化研究进展

孟娜^a, 刘启顺^a, 刘瑞生^a, 吕玉芬^a^,^*(), 赵晓辉^b^,^*(), 魏伟^a^,^b^,^*()

a 曲阜师范大学化学与化工学院山东曲阜 273165
b 中国科学院西北高原生物研究所中国科学院藏药研究重点实验室青海西宁 810008

收稿日期:2021-07-07 修回日期:2021-07-29 发布日期:2021-08-09
通讯作者: 吕玉芬, 赵晓辉, 魏伟
作者简介:
† 共同第一作者
基金资助:
山东省高校青创科技计划(2019KJC021); 2018中国科学院“西部之光”人才培养引进计划资助项目

Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones

Na Meng^a, Qishun Liu^a, Ruisheng Liu^a, Yufen Lü^a(), Xiaohui Zhao^b(), Wei Wei^a^,^b()

a School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
b Key Laboratory of Tibetan Medicine Research, Chinese Academy of Sciences, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, Qinghai 810008

Received:2021-07-07 Revised:2021-07-29 Published:2021-08-09
Contact: Yufen Lü, Xiaohui Zhao, Wei Wei
About author:
† These authors contributed equally to this work.
Supported by:
Youth Innovation and Technology Project of Higher School in Shandong Province(2019KJC021); 2018 CAS "Light of West China" Program

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摘要/Abstract

芳基和砜基化合物在合成化学、药物化学、材料化学等领域具有广泛的应用价值. 因此, 其清洁、高效的构建方法备受人们的关注. 芳基偶氮砜在光、电或热条件下可以发生C—N和S—N键均裂, 产生芳基和砜基自由基, 进而发生芳基化或砜基化反应选择性构建芳基或砜基化合物. 归纳总结了近年来芳基偶氮砜参与的芳基化及砜基化反应最新研究进展, 重点介绍了其合成方法及反应机理, 并对该领域的未来发展进行了展望.

关键词: 芳基偶氮砜, 光催化, 电催化, 芳基化, 砜基化

Aromatic ring- and sulfone-containing compounds are widely used in the fields of synthetic chemistry, medicinal chemistry and material chemistry. Therefore, it is of great significance to develop a simple, green and efficient method to construct aryl and sulfonyl compounds. Arylazo sulfones can be used as arylation or sulfonylation reagents to access aryl and sulfonyl compounds via hemolytic cleavage of C—N and N—S bonds to generate aryl radical and sulfonyl radical. In this review, the recent research progress of arylations and sulfonylations using arylazo sulfones is summarized. The synthetic methods and the related reaction mechanisms are highlighted, and an outlook of this research field is also given.

Key words: arylazo sulfones, photocatalysis, electrocatalytic, arylations, sulfonylations

引用此文

孟娜, 刘启顺, 刘瑞生, 吕玉芬, 赵晓辉, 魏伟. 芳基偶氮砜的芳基化及砜基化研究进展[J]. 有机化学, 2021, 41(12): 4639-4650.

Na Meng, Qishun Liu, Ruisheng Liu, Yufen Lü, Xiaohui Zhao, Wei Wei. Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4639-4650.

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图/表 30

图式1. 芳基偶氮砜的芳基化和砜基化反应应用

Scheme 1. Application of arylazo sulfones for arylations and sulfonations

图式2. 常见的芳基化合物合成方法

Scheme 2. General methods for the synthesis of aryl compounds

图式3. 光促进芳基偶氮砜与芳香环/芳香杂环的芳基化反应

Scheme 3. Visible-light-induced arylation reaction of arylazo sulfones with aromatic/heteroaromatic ring

图式4. 芳基偶氮砜与芳香环/芳香杂环的芳基化反应机理

Scheme 4. Reaction mechanism for arylation reaction of arylazo sulfones with aromatic/heteroaromatic ring

图式5. 芳基偶氮砜和烯丙基砜反应构建烯丙基取代芳烃

Scheme 5. Reaction of arylazo sulfones with allyl sulfones to construct allyl arenes

图式6. 光诱导芳基偶氮砜和芳基硼酸反应构建联苯类化合物

Scheme 6. Visible-light-induced reaction of arylazo sulfones with arylboronic acids to construct (hetero)biaryls

图式7. 芳基偶氮砜和芳基硼酸反应机理

Scheme 7. Reaction mechanism for arylation reaction of arylazo sulfones with arylboronic acids

图式8. 可见光诱导下芳基偶氮砜和异腈反应构建取代的芳香酰胺

Scheme 8. Visible-light-induced reaction of arylazo sulfones with isonitriles to construct aromatic amides

图式9. 芳基偶氮砜和异腈反应构建芳香酰胺的反应机理

Scheme 9. Reaction mechanism for the synthesis of aromatic amides from arylazo sulfones and isonitriles

图式10. 光介导下芳基偶氮砜和1,1-二芳基乙烯反应构建三芳基乙烯

Scheme 10. Visible-light-induced reaction of arylazo sulfones with 1,1-diarylethylenes to construct triarylethylenes

图式11. 光介导下芳基偶氮砜和联硼酸频那醇酯反应

Scheme 11. Visible-light-induced reaction of arylazo sulfones and B2pin2

图式12. 光介导下芳基偶氮砜和联硼酸频那醇酯反应构建芳基硼酸酯的反应机理

Scheme 12. Reaction mechanism for the visible light induced synthesis of arylboronates form arylazo sulfones and bis(pinacolato)diboron

图式13. 光诱导芳基偶氮砜与喹喔啉酮芳基化反应

Scheme 13. Visible-light-induced arylations of quinoxalin- 2(1H)-ones with arylazo sulfones

图式14. 芳基偶氮砜与喹喔啉酮芳基化反应可能的机理

Scheme 14. The possible reaction mechanism for the arylations of quinoxalin-2(1H)-ones with arylazo sulfones

图式15. 光诱导下芳基偶氮砜和六甲基二锡烷反应构建芳基锡化合物

Scheme 15. Visible-light-induced reaction of arylazo sulfones with hexaalkyldistannanes to construct (hetero)arylstannanes

图式16. 光诱导下芳基偶氮砜与六甲基二锡烷反应构建芳基锡化合物反应机理

Scheme 16. Reaction mechanism for the arylations of hexaalkyldistannanes with arylazo sulfones to construct (hetero)- arylstannanes

图式17. 光诱导芳基偶氮砜和亚磷酸酯反应构建芳基磷酸酯

Scheme 17. Visible-light-induced reaction of arylazo sulfones with phosphites to construct arylphosphonates

图式18. 芳基偶氮砜与亚磷酸酯反应构建芳基磷酸酯的反应机理

Scheme 18. Reaction mechanism for arylations of phosphites with arylazo sulfones to construct aryl phosphonates

图式19. 光诱导芳基偶氮砜和硫酚反应构建不对称亚砜化合物

Scheme 19. Visible-light-induced reaction of arylazo sulfones and thiols to construct unsymmetrical sulfoxides

图式20. 合成不对称亚砜的反应机理

Scheme 20. Reaction mechanism for the synthesis of unsymmetrical sulfoxides

图式21. 电催化芳基偶氮砜与硫酚反应合成硫醚

Scheme 21. Electrocatalytic synthesis of thioethers from arylazo sulfones and thiols

图式22. 电催化芳基偶氮砜与联硼酸频那醇酯反应合成芳基硼酸酯

Scheme 22. Electrocatalytic synthesis of aryl borates from arylazo sulfones and B2pin2

图式23. 光诱导烯烃与芳基偶氮砜和氧气反应构建β-羰基砜

Scheme 23. Visible-light-induced reaction of alkenes with arylazo sulfones and dioxygen to construct β-keto sulfones

图式24. 烯烃氧砜化反应合成β-羰基砜的反应机理

Scheme 24. Reaction mechanism for oxysulfonylation of alkenes to construct β-keto sulfones

图式25. 光诱导芳基偶氮砜和炔烃反应构建β-羰基砜

Scheme 25. Visible-light-induced reaction of arylazo sulfones and alkynes to construct β-keto sulfones

图式26. 炔烃氧砜化反应合成β-羰基砜的反应机理

Scheme 26. Reaction mechanism for oxysulfonylation of alkynes to construct β-keto sulfones

图式27. 芳基偶氮砜和肉桂酸反应构建E-烯基砜

Scheme 27. Reaction of arylazo sulfones and cinnamic acids to construct (E)-vinyl sulfones

图式28. 芳基偶氮砜和肉桂酸砜化反应机理

Scheme 28. Reaction mechanism for sulfonylation of cinnamic acids with arylazo sulfones

图式29. 芳基偶氮砜和1,6-烯炔砜化/环化反应构建砜代γ-丁内酰胺

Scheme 29. Sulfonylation/cyclization of 1,6-enynes with arylazo sulfones leading to sulfonylated γ-butyrolactams

图式30. 合成砜代γ-丁内酰胺的反应机理

Scheme 30. Reaction mechanism for the synthesis of sulfonylated γ-butyrolactams

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芳基偶氮砜的芳基化及砜基化研究进展

Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones

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