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

doi:10.6023/cjoc202210013

有机化学 ›› 2022, Vol. 42 ›› Issue (12): 3959-3978.DOI: 10.6023/cjoc202210013 上一篇下一篇

所属专题：自由基化学专辑

综述与进展

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)

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摘要/Abstract

芳基重氮盐以其较高的反应活性和广泛的来源, 被广泛应用于有机合成中. 芳基重氮盐作为一种常见的亲电试剂通过保留N₂骨架和离去N₂, 在材料化学、染料化学和药物化学等领域有着非常广泛的应用. 近些年, 随着自由基化学的迅速发展, 利用芳基重氮盐产生芳基自由基参与的环化反应也得到了迅速的发展. 整理了近十年来关于芳基重氮盐产生芳基自由基参与的环化反应的文献, 从芳基自由基对不饱和碳碳键、碳氮键的加成后构建各种环状化合物进行归纳. 最后, 对目前的研究进展进行了总结.

关键词: 芳基重氮盐, 芳基自由基, 不饱和键, 环化反应

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

引用此文

姜松, 南宁, 何景昊, 郭嘉程, 秦景灏, 谢叶香, 欧阳旋慧, 宋仁杰. 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[J]. 有机化学, 2022, 42(12): 3959-3978.

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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图/表 45

图式1. 可见光诱导的肉桂酸的脱羧环氧化反应

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

图式2. 金催化体系下芳基重氮盐参与的烯烃环化反应

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

图式3. 可见光介导的N-芳基丙烯酰胺的环化反应

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

图式4. 不同催化体系下N-芳基丙烯酰胺参与的环化反应

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

图式5. 不同催化体系下芳基自由基参与的内酯化反应

Scheme 5. Lactonization of aryl radical under different catalytic systems

图式6. 2-(烯丙氧基)自由基参与的环化反应

Scheme 6. Cyclization of 2-(allyloxy) radical

图式7. 光催化的烯基环醇的开环反应

Scheme 7. Photocatalytic ring-opening reaction of alkenyl cyclitol

图式8. 联烯酯与芳基重氮盐的芳基化/环化反应

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

图式9. 光驱动的金/光氧化还原双催化芳基化级联反应

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

图式10. β-炔基丙烯酮的多组分环化反应及机理

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

图式11. 多取代吡唑的合成

Scheme 11. Synthesis of polysubstituted pyrazoles

图式12. 3-磺化-2H-吡咯-2-酮的简易合成

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

图式13. 二氧化硫参与的1,5二烯与芳基重氮盐的环化反应

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

图式14. 1,5-二烯、芳基重氮盐和DABCO?(SO2)2的串联磺酰化/环化反应

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

图式15. 异色酮的合成

Scheme 15. Synthesis of isochromanones

图式16. 异黄酮的合成

Scheme 16. Synthesis of isoflavones

图式17. 铜催化芳基重氮盐、DABCO(SO2)2和二烯的Heck型环化反应

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

图式18. 光催化N-苄基丙烯酰胺的环化反应及机理

Scheme 18. Photocatalyzed cyclization and mechanism of N-benzylacrylamides

图式19. N-芳基丙炔酰胺和N-苄基丙烯酰胺的自由基级联螺旋环化反应

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

图式20. 无金属催化1,6-烯炔的自由基级联环化反应

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

图式21. 1,7-烯炔与芳基重氮盐的自由基环化反应

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

图式22. 4-甲氧基苯胺与1,7-烯炔的自由基脱氨环化反应

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

图式23. 自由基诱导的无金属[2+2]环加成和自由基1,4-加成反应

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

图式24. 磺酰化吲哚[2,1-a]异喹啉的合成

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

图式25. 光催化苯并噻吩的合成

Scheme 25. Photocatalytic synthesis of benzothiophenes

图式26. 金/光氧化还原双催化炔烃分子内的亲核环化反应

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

图式27. 炔烃双芳基化合成2,3-二氢吡咯和吲哚

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

图式28. 不同催化体系下取代吲哚的合成

Scheme 28. Synthesis of substituted indole under different systems

图式29. 不同催化体系下β-炔基酮的环化反应

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

图式30. 光氧化还原和金催化协同的1,6-烯炔与芳基重氮盐的芳基环化反应

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

图式31. 3-磺化香豆素的合成

Scheme 31. Synthesis of 3-sulfonated coumarins

图式32. 金/光氧化还原催化含杂原子炔烃的环化反应

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

图式33. 磺化四氢吡啶衍生物的合成

Scheme 33. Synthesis of sulfonated tetrahydropyridine derivatives

图式34. 金催化炔烃的芳基碳环化反应

Scheme 34. Gold-catalyzed arylative carbocyclization of alkynes

图式35. 3-芳基磺酰化硫黄酮的合成

Scheme 35. Synthesis of 3-arylsulfonylated thioflavones

图式36. 磺酰化二苯并氮平衍生物的合成

Scheme 36. Synthesis of sulfonylated dibenzazepine derivatives

图式37. 光催化9,10-二取代菲类化合物的合成

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

图式38. 双SO2插入的苯联1,7-二炔的多组分环化级联反应

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

图式39. 可见光催化N-丙炔吲哚的环化反应

Scheme 39. Visible light catalyzed cyclization of N-propargylindoles

图式40. 邻螺旋环己二烯酮的合成

Scheme 40. Synthsis of ortho-spirocyclo hexadienones

图式41. 可见光促进的金/光氧化还原双催化芳基烷基酸酯的环化反应

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

图式42. 可见光促进N-芳基丙炔酰胺的磺酰化反应

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

图式43. 光催化邻异氰基-α-溴肉桂酸酯的串联环化反应

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

图式44. 菲啶衍生物的无过渡金属合成

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

图式45. 2-异氰联苯与胺的电化学偶联反应

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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