Recent Progress in Radical Arylation Reaction Involving Diaryliodonium Salts

doi:10.6023/cjoc202412026

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3672-3690.DOI: 10.6023/cjoc202412026 Previous Articles Next Articles

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二芳基碘盐参与的自由基芳基化反应研究进展

诸雨楠^a, 矫伟康^a, 韦雪白^a, 陈春华^a^,^*(), 莫冬亮^b^,^*()

^a 广西民族大学化学化工学院林产化学与工程国家民委重点实验室广西林产化学与工程重点实验室林木生物质低碳高质利用广西高校工程研究中心南宁 530006
^b 广西师范大学化学与药学学院广西桂林 541004

收稿日期:2024-12-25 修回日期:2025-03-28 发布日期:2025-04-16
基金资助:
广西民族大学人才引进(2022KJQD14); 广西科技基地与人才专项(AD23026046); 广西壮族自治区级大学生创新训练计划(S202410608069)

Recent Progress in Radical Arylation Reaction Involving Diaryliodonium Salts

Yu'nan Zhu^a, Weikang Jiao^a, Xuebai Wei^a, Chunhua Chen^a^,^*(), Dongliang Mo^b^,^*()

^a Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi University Engineering Research Center of Low-carbon and High-quality Utilization of Forest Biomass, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006
^b School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004

Received:2024-12-25 Revised:2025-03-28 Published:2025-04-16
Contact: * Chenchunhua@gxmzu.edu.cn; moeastlight@mailbox.gxnu.edu.cn
Supported by:
Guangxi Minzu University Scientific Research Funds for Talent Introduction(2022KJQD14); Guangxi Science and Technology Base and Talent Special Project(AD23026046); Student Innovation Training Program of Guangxi Zhuang Autonomous Region(S202410608069)

Diaryliodonium salts, which serve as highly electrophilic arylation reagents, have been widely used in organic synthetic chemistry due to their environmental compatibility, remarkable stability, and excellent selectivity. As novel reagents, they can produce aryl radicals to synthesize aromatic compounds. The research progress achieved in the past decade regarding the construction of carbon-carbon and carbon-heteroatom bonds by utilizing aryl radicals derived from diaryliodonium salts is summarized with content mainly divided into two parts: arylation induced by visible light and arylation without photocatalysis. Their applications in the synthesis of bioactive arylated heterocyclic compounds are also discussed.

Key words: radical reaction, arylation, diaryliodonium salt, heterocyclic compound, photocatalysis

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Yu'nan Zhu, Weikang Jiao, Xuebai Wei, Chunhua Chen, Dongliang Mo. Recent Progress in Radical Arylation Reaction Involving Diaryliodonium Salts[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3672-3690.

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Fig. & Tab. 44

Scheme 1. Types of radical arylation reactions by diaryliodo- nium salts

Scheme 2. Pd/Ir-catalyzed C—H arylation of diaryliodonium salts

Scheme 3. Visible light-mediated arylation of arenes and heteroarenes with diaryliodonium salts

Scheme 4. Oxyarylation and aminoarylation of styrenes using photoredox catalysis

Scheme 5. Intermolecular multicomponent oxyarylation of alkenes for the synthesis of α-arylated ether

Scheme 6. Visible light-promoted synthesis of isoquinolines from vinyl isocyanides and diaryliodonium salts

Scheme 7. Photocatalytic acylarylation of unactivated alkenes with diaryliodonium salts

Scheme 8. Visible light accelerated vinyl C—H arylation via Pd-catalysis

Scheme 9. Photocatalyst-free aryl radical reaction from diaryliodonium salts

Scheme 10. Arylation of arenes and heteroarenes with diaryliodonium salts by photoredox catalysis

Scheme 11. Visible-light-mediated arylation of ortho-hydroxy- arylenaminones

Scheme 12. Synthesis of (±)-Norascyronone A by photoredox-catalyzed cascade reactions involving aryl radical

Scheme 13. Visible light photoredox-catalyzed arylation of quinoxalin-2(1H)-ones with diaryliodonium salts

Scheme 14. Visible light photoredox-catalyzed arylative cycli- zation to access benzimidazo[2,1-a]isoquinolin-6(5H)-ones

Scheme 15. Ru-photoredox-catalyzed arylative radical cascades to furnish functionalized pyrazolones

Scheme 16. Visible-light-promoted arylation of quinoline and pyridine N-oxides with diaryliodonium salts

Scheme 17. Photoinduced aryl radical cascade for the synthesis of quaternary CF3-containing 2-oxindoles

Scheme 18. Organophotoredox-catalyzed arylation of acetates with diaryliodonium reagents

Scheme 19. Electron donor-acceptor photoactivation involving diaryliodonium reagents

Scheme 20. Novel electron donor-acceptor complexes (EDA) promoted arylation under visible light irradiation

Scheme 21. Synthesis of thiophosphates through three-component reaction under visible light irradiation

Scheme 22. Visible-light photoredox-catalyzed aminosulfonylation of diaryliodonium salts with SO2 and hydrazines

Scheme 23. Sulfoxidation of organic sulfidation reagents via photocatalysis

Scheme 24. Synthesis of 3-arylsulfonylquinoline derivatives via visible-light-induced multicomponent cascade cyclization

Scheme 25. Synthesis of sulfonylated coumarins via three component reaction mediated by visible light

Scheme 26. Synthesis of sulfonylated oxindoles via three component reaction induced by visible light

Scheme 27. Three-component coupling of thiols, iodonium salts and DABSO

Scheme 28. Sulfonylation of various pyrrolo [1,2-a]pyridines under visible-light

Scheme 29. Visible light mediated reaction of N-arylpropiol- amides and diaryiodonium salts

Scheme 30. Synthesis of arylsulfonyl fluoride via organophotocatalytic fluorosulfonylation of diaryliodonium salts

Scheme 31. Organophotoredox-catalyzed aryl sulfonylation of diaryliodonium reagents

Scheme 32. Photoredox-catalyzed sulfonylation of diaryliodonium salts with DABSO and silyl enolates

Scheme 33. Photoactivation of diaryliodonium reagents to synthesis of chalcogenides

Scheme 34. Ru-photoredox-catalyzed radical cascades of aryl sulfonylative to furnish functionalized pyrazolones

Scheme 35. Visible-light-mediated metal-free synthesis of aryl phosphonates

Scheme 36. Arylation of tertiary phosphines with diaryliodonium triflates

Scheme 37. EDA-complex initiated phosphorus arylation of diaryliodonium salts to synthesize phosphine oxides

Scheme 38. Oxyarylation of diaryliodonium tetrafluoroborates and styrenes

Scheme 39. Direct α-selective arylation of difluoroboronates via base-mediated C—H functionalization

Scheme 40. Construction of functionalized annulated sulfones from cyclic diaryliodonium salts

Scheme 41. Wet salt carbonate-promoted radical arylation of vinyl pinacolboronates with diaryliodonium salts

Scheme 42. Aryl radical-induced desulfonylative ipsosubstitution of diaryliodonium salts

Scheme 43. Palladium-catalyzed C(2)-arylation/intramolecular acylation of arylcarboxylic acids

Scheme 44. O-Arylation and [3,3]-rearrangement for synthesis of 3-(2-hydroxyaryl)indazoles

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二芳基碘盐参与的自由基芳基化反应研究进展

Recent Progress in Radical Arylation Reaction Involving Diaryliodonium Salts

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