Recent Progress in Aryl Radical-Mediated Cyclization of Unsaturated Bonds Based on Aryldiazonium Salts

doi:10.6023/cjoc202210013

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 3959-3978.DOI: 10.6023/cjoc202210013 Previous Articles Next Articles

Special Issue: 自由基化学专辑

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基于芳基重氮盐的芳基自由基介导的不饱和键环化反应研究进展

姜松^a, 南宁^a, 何景昊^a, 郭嘉程^a, 秦景灏^a^,^*(), 谢叶香^a, 欧阳旋慧^a^,^c^,^*(), 宋仁杰^a^,^b^,^c^,^*()

a 江西省持久性污染物控制与资源循环利用重点实验室南昌 330063
b 化学生物传感与计量学国家重点实验室长沙 410082
c 江西省金属材料微结构调控重点实验室南昌 330063

收稿日期:2022-10-14 修回日期:2022-11-18 发布日期:2022-11-28
通讯作者: 秦景灏, 欧阳旋慧, 宋仁杰
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(51878326); 国家自然科学基金(21861027); 国家自然科学基金(22161030); 国家自然科学基金(21901100); 江西省自然科学基金(20212ACB203007); 江西省自然科学基金(20204BCJ23010); 江西省自然科学基金(20202ACBL216017); 江西省自然科学基金(20212AEI91002); 江西省自然科学基金(20202ACB203002); 国家重点实验室专项课题经费(SKLCBSC-2021019)

Recent Progress in Aryl Radical-Mediated Cyclization of Unsaturated Bonds Based on Aryldiazonium Salts

Song Jiang^a, Ning Nan^a, Jinghao He^a, Jiacheng Guo^a, Jinghao Qin^a(), Yexiang Xie^a, Xuanhui Ouyang^a^,^c(), Renjie Song^a^,^b^,^c()

a Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang 330063
b State Key Laboratory of Chemo/Biosensing and Chemometrics, Changsha 410082
c Key Laboratory for Microstructural Control of Metallic Materials of Jiangxi Province, Nanchang 330063

Received:2022-10-14 Revised:2022-11-18 Published:2022-11-28
Contact: Jinghao Qin, Xuanhui Ouyang, Renjie Song
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(51878326); National Natural Science Foundation of China(21861027); National Natural Science Foundation of China(22161030); National Natural Science Foundation of China(21901100); Natural Science Foundation of Jiangxi Province(20212ACB203007); Natural Science Foundation of Jiangxi Province(20204BCJ23010); Natural Science Foundation of Jiangxi Province(20202ACBL216017); Natural Science Foundation of Jiangxi Province(20212AEI91002); Natural Science Foundation of Jiangxi Province(20202ACB203002); Special Project Funds of State Key Laboratory(SKLCBSC-2021019)

Aryldiazonium salts are widely used in organic synthesis due to their high reactivity and readily availability. As a common arylation reagent, aryl diazonium salts have been widely used in material chemistry, dye chemistry and medicinal chemistry by retaining and leaving N₂ skeleton. In recent years, with the rapid development of radical chemistry, the cyclization reaction involving aryl radicals, which produced by aryldiazonium salts, has also been developed rapidly, and this strategy also stimulates the enthusiasm of organic chemists to construct various ring compounds. In this review, the addition of unsaturated carbon-carbon bonds and carbon-nitrogen bonds to construct various cyclic compounds from aryl radicals is summarized and classified according to the size of the cyclic compounds. Finally, the current research progress is summarized.

Key words: aryl diazonium salts, aryl radical, unsaturated bonds, cyclization

Cite this article

Song Jiang, Ning Nan, Jinghao He, Jiacheng Guo, Jinghao Qin, Yexiang Xie, Xuanhui Ouyang, Renjie Song. Recent Progress in Aryl Radical-Mediated Cyclization of Unsaturated Bonds Based on Aryldiazonium Salts[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 3959-3978.

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Fig. & Tab. 45

Scheme 1. Visible-light-induced decarboxylative epoxidation of trans-cinnamic acids

Scheme 2. Gold-catalyzed cyclization of olefin with aryl diazonium salts

Scheme 3. Visible-light mediated cyclization of N-arylacryl- amides

Scheme 4. Cyclization of N-arylacrylamides under different catalytic systems

Scheme 5. Lactonization of aryl radical under different catalytic systems

Scheme 6. Cyclization of 2-(allyloxy) radical

Scheme 7. Photocatalytic ring-opening reaction of alkenyl cyclitol

Scheme 8. Arylation/cyclization of allenylic esters with aryl diazonium salts

Scheme 9. Light-driven dual gold/photoredox catalysis for arylation cascade

Scheme 10. Multi-component cyclization and mechanism of β-alkynyl propenones

Scheme 11. Synthesis of polysubstituted pyrazoles

Scheme 12. Facile synthesis of 3-sulfonated 2H-pyrrol-2-ones

Scheme 13. Cyclization of 1,5-dienes with aryl diazonium salts involing SO2

Scheme 14. Tandem sulfonylation/cyclization of 1,5-diene, aryldiazonium salt and DABCO?(SO2)2

Scheme 15. Synthesis of isochromanones

Scheme 16. Synthesis of isoflavones

Scheme 17. Copper-catalyzed Heck type cyclization of aryl diazonium salts, DABCO(SO2)2 and 1,7-dienes

Scheme 18. Photocatalyzed cyclization and mechanism of N-benzylacrylamides

Scheme 19. Radical cascade spirocyclizations of N-arylpro- piolamides and N-benzylacrylamides

Scheme 20. Metal-free radical cascade cyclization of 1,6-enynes

Scheme 21. Cyclization of 1,7-enynes with aryldiazonium salt

Scheme 22. Radical deaminative cyclization of 4-methoxy- anilines with 1,7-enynes

Scheme 23. Radical-induced metal-free [2+2] cycloaddition and 1,4-addition

Scheme 24. Synthesis of sulfonylated indolo[2,1-a]isoquino- lines

Scheme 25. Photocatalytic synthesis of benzothiophenes

Scheme 26. Gold/photoredox dual catalysis for intramolecular nucleophilic cyclization of alkyne

Scheme 27. Diarylation of alkynes to form 2,3-dihydropyrroles and indoles

Scheme 28. Synthesis of substituted indole under different systems

Scheme 29. Cyclization of β-alkynyl ketones under different catalytic systems

Scheme 30. Cyclization of 1,6-enyne with aryl diazonium salts enabled synergistic photocatalyst and gold-catalyst

Scheme 31. Synthesis of 3-sulfonated coumarins

Scheme 32. Gold/photoredox catalyzed cyclization of heteroatom tethered alkynes

Scheme 33. Synthesis of sulfonated tetrahydropyridine derivatives

Scheme 34. Gold-catalyzed arylative carbocyclization of alkynes

Scheme 35. Synthesis of 3-arylsulfonylated thioflavones

Scheme 36. Synthesis of sulfonylated dibenzazepine derivatives

Scheme 37. Photocatalytic synthesis of 9,10-disubstituted phenanthrenes

Scheme 38. Double SO2 insertion multicomponent cyclization cascade of benzene-linked 1,7-diynes

Scheme 39. Visible light catalyzed cyclization of N-propargylindoles

Scheme 40. Synthsis of ortho-spirocyclo hexadienones

Scheme 41. Visible-light-promoted dualgold/photoredox catalysis for cyclization of aryl-alkynoates

Scheme 42. Visible-light-promoted sulfonylation of N-arylpropiolamide

Scheme 43. Photocatalyzed tandem cyclization of ortho-isocyano-α-bromo cinnamates

Scheme 44. Transition-metal-free synthesis of phenanthridine derivatives

Scheme 45. Electrochemical coupling of 2-isocyanobiphenyls and amines

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基于芳基重氮盐的芳基自由基介导的不饱和键环化反应研究进展

Recent Progress in Aryl Radical-Mediated Cyclization of Unsaturated Bonds Based on Aryldiazonium Salts

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[3]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
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