Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones

doi:10.6023/cjoc202107022

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4639-4650.DOI: 10.6023/cjoc202107022 Previous Articles Next Articles

Special Issue: 绿色合成化学专辑；热点论文虚拟合集

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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

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

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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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Fig. & Tab. 30

Scheme 1. Application of arylazo sulfones for arylations and sulfonations

Scheme 2. General methods for the synthesis of aryl compounds

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 20. Reaction mechanism for the synthesis of unsymmetrical sulfoxides

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

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

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

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

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

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

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

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

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

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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