二芳基碘盐参与的自由基芳基化反应研究进展

doi:10.6023/cjoc202412026

有机化学 ›› 2025, Vol. 45 ›› Issue (10): 3672-3690.DOI: 10.6023/cjoc202412026 上一篇下一篇

综述与进展

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)

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摘要/Abstract

二芳基碘盐作为一类高度亲电的芳基化试剂, 因其具有环境友好、稳定性好及选择性高等优点, 在有机合成化学中得到了广泛应用. 它是一种可以产生芳基自由基来合成芳香族化合物的新型试剂. 综述了近十年来二芳基碘盐通过芳基自由基过程构建碳-碳键和碳-杂键等新键的研究进展, 内容主要分为可见光诱导和无光照催化两部分, 并讨论了它们在合成具有生物活性的芳基化合物中的应用.

关键词: 自由基反应, 芳基化, 二芳基碘盐, 杂环化合物, 光催化

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

引用此文

诸雨楠, 矫伟康, 韦雪白, 陈春华, 莫冬亮. 二芳基碘盐参与的自由基芳基化反应研究进展[J]. 有机化学, 2025, 45(10): 3672-3690.

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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图/表 44

图式1. 二芳基碘盐参与的自由基芳基化反应类型

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

图式2. 钯/铱催化二芳基碘盐的C—H芳基化反应

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

图式3. 可见光介导的芳烃和杂芳烃与二芳基碘盐的芳化反应

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

图式4. 光氧化还原催化苯乙烯的氧化芳基化和氨化芳基化

Scheme 4. Oxyarylation and aminoarylation of styrenes using photoredox catalysis

图式5. 烯烃分子间多组分氧化芳基化反应合成α-芳基醚

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

图式6. 异腈酸乙烯与二芳基碘盐在可见光促进下反应合成异喹啉

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

图式7. 非活化烯烃与二芳基碘盐的光催化酰基化反应

Scheme 7. Photocatalytic acylarylation of unactivated alkenes with diaryliodonium salts

图式8. 钯和可见光加速的乙烯基C—H芳基化反应

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

图式9. 二芳基碘盐在无光催化剂条件下的芳基自由基反应

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

图式10. 光氧化还原催化芳烃和杂芳烃与二芳基碘盐的芳基化反应

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

图式11. 可见光介导邻羟基烯胺酮的芳基化反应

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

图式12. 涉及芳基自由基的光氧化催化级联反应合成(±)- Norascyronone A

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

图式13. 可见光光氧化催化喹啉-2-(1H)酮与二芳基碘盐的芳基化反应

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

图式14. 可见光光氧化催化芳基环化构建苯并咪唑[2,1-a]异喹啉-6(5H)-酮

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

图式15. 钌光氧化还原催化芳基自由基串联合成官能团化吡唑酮

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

图式16. 可见光促进喹啉和吡啶N-氧化物与二芳基碘盐的芳基化反应

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

图式17. 光诱导芳基自由基级联反应合成含CF3的2-吲哚酮

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

图式18. 有机光氧化还原催化乙酸酯与二芳基碘试剂的芳基化反应

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

图式19. 二芳基碘盐参与的电子供体-受体光活化反应

Scheme 19. Electron donor-acceptor photoactivation involving diaryliodonium reagents

图式20. 新型电子供体-受体配合物(EDA)在可见光下促进的芳基化

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

图式21. 可见光照射的三组分反应合成硫代磷酸盐

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

图式22. 可见光光氧化还原催化二芳基碘盐、肼和二氧化硫的氨磺酰化反应

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

图式23. 光催化有机硫化试剂的亚砜化反应

Scheme 23. Sulfoxidation of organic sulfidation reagents via photocatalysis

图式24. 可见光诱导多组分级联环化合成3-芳基磺酰喹啉衍生物

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

图式25. 可见光介导的三组分反应合成磺化香豆素

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

图式26. 可见光诱导下的三组分反应合成磺化吲哚酮

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

图式27. 硫酚、二芳基碘盐和DABSO的三组分偶联反应

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

图式28. 可见光介导的各种吡咯[1,2-a]吡啶的磺化反应

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

图式29. 可见光介导N-芳基丙炔酰胺与二芳基碘盐的反应

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

图式30. 有机光催化二芳基碘盐的氟磺化反应合成芳基磺酰氟

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

图式31. 有机光氧化还原催化二芳基碘试剂的芳磺酰化反应

Scheme 31. Organophotoredox-catalyzed aryl sulfonylation of diaryliodonium reagents

图式32. 光氧化还原催化二芳基碘盐、DABSO和硅基烯醇化物的磺酰化反应

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

图式33. 二芳基碘盐试剂在光活化作用下合成硫醚化合物

Scheme 33. Photoactivation of diaryliodonium reagents to synthesis of chalcogenides

图式34. 钌光氧化催化芳磺酰腙的自由基级联反应生成功能化吡唑酮

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

图式35. 无金属可见光介导芳基膦酸盐的合成.

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

图式36. 叔膦与三氟甲磺酸二芳基碘盐的芳基化反应

Scheme 36. Arylation of tertiary phosphines with diaryliodonium triflates

图式37. 电子供体-受体配合物引发二芳基碘盐的磷芳基化反应合成氧化膦

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

图式38. 四氟硼酸二芳基碘盐与苯乙烯的氧化芳基化反应

Scheme 38. Oxyarylation of diaryliodonium tetrafluoroborates and styrenes

图式39. 碱介导的C—H官能化合成α-选择性芳基化二氟硼化物

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

图式40. 环二芳基碘盐构建功能化环砜

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

图式41. 湿碳酸盐促进烯基嚬哪醇硼酸酯和二芳基碘盐的自由基芳基化反应

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

图式42. 芳基自由基诱导二芳基碘盐的异位取代反应

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

图式43. 钯催化芳基羧酸的C(2)-芳基化/分子内酰化反应

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

图式44. O-芳基化/[3,3]重排反应合成2-羟基芳基吲唑

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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