芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展

doi:10.6023/cjoc202102014

有机化学 ›› 2021, Vol. 41 ›› Issue (7): 2587-2600.DOI: 10.6023/cjoc202102014 上一篇下一篇

综述与进展

芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展

张永红^a^,^b^,^*(), 唐承宗^a, 刘永红^a, 刘晨江^a^,^b^,^*()

a 新疆大学化学学院省部共建碳基能源资源化学与利用国家重点实验室石油天然气精细化工教育部&自治区重点实验室乌鲁木齐绿色催化与合成技术重点实验室乌鲁木齐 830046
b 北京分子科学国家研究中心北京 100871

收稿日期:2021-02-02 修回日期:2021-03-23 发布日期:2021-04-16
通讯作者: 张永红, 刘晨江
基金资助:
新疆维吾尔自治区自然科学基金(2017D01C035); 国家自然科学基金(21762041); 国家自然科学基金(21861036)

Research Progress of Aryltriazene as Aryl Precursor and Aryl-Azo Precursors in Organic Synthesis

Yonghong Zhang^a^,^b(), Chengzong Tang^a, Yonghong Liu^a, Chenjiang Liu^a^,^b()

a State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830046
b Beijing National Laboratory for Molecular Sciences, Beijing 100871

Received:2021-02-02 Revised:2021-03-23 Published:2021-04-16
Contact: Yonghong Zhang, Chenjiang Liu
Supported by:
Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2017D01C035); National Natural Science Foundation of China(21762041); National Natural Science Foundation of China(21861036)

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摘要/Abstract

芳基三氮烯因制备简单, 稳定性好, 反应位点多, 反应条件温和等优点, 作为一种稳定的芳基重氮盐替代物被广泛用于有机合成中. 主要综述了近年来以芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展.

关键词: 芳基三氮烯, 芳基前体, 芳基偶氮前体, 有机合成方法学

Aryltriazenes have been widely used as a stable aryldiazonium salt surrogate in organic synthesis, in which the compounds show advantages of easy preparation, good stability, multiple reaction sites and mild reaction conditions. In this review, the recent advances in the application of aryltriazenes in organic synthesis as aryl or aryl azo precursors are reviewed.

Key words: aryl triazene, aryl precursor, aryl azo precursor, organic synthetic methodology

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张永红, 唐承宗, 刘永红, 刘晨江. 芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展[J]. 有机化学, 2021, 41(7): 2587-2600.

Yonghong Zhang, Chengzong Tang, Yonghong Liu, Chenjiang Liu. Research Progress of Aryltriazene as Aryl Precursor and Aryl-Azo Precursors in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2587-2600.

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图/表 26

图1. 芳基三氮烯的结构及反应位点

Figure 1. Structure and the reaction sites of ayltriazene

图式1. 芳基三氮烯常见合成方法

Scheme 1. Common synthetic methods of aryltriazene

图2. 活化芳基三氮烯的促进剂或催化剂及其活化模式

Figure 2. Promoter or catalyst used for activation of aryltriazene and their activation mode

图式2. 芳基三氮烯作为芳基前体或芳基偶氮前体在有机合成中的应用

Scheme 2. Aryltriazene as aryl and aryl-azo precursor in organic synthesis

图式3. 近年来芳基三氮烯作为芳基前体在有机合成中的应用

Scheme 3. Applacation of aryltriazene as aryl precursor in organic synthesis in recent years

图式4. 芳基三氮烯与肉桂酸的脱羧偶联反应

Scheme 4. Decarboxylative coupling of aryltriazene with cinnamic acid

图式5. 烯/炔烃与芳基三氮烯的Heck/Sonogashira偶联反应

Scheme 5. Heck/Sonogashira coupling reactions of aryltriazenes with styrenes and aryl/alkyl acetylenes

图式6. 炔烃与芳基三氮烯的氧化交叉偶联反应

Scheme 6. Oxidative cross-coupling reactions of alkynes and aryl triazenes

图式7. 无外加配体条件下芳基三氮烯与芳基硼酸的Suzuki- Miyaura偶联反应

Scheme 7. Additional ligand-free Suzuki-Miyaura cross-coup- ling reactions of aryltriazenes with arylboronic acid

图式8. 芳基三氮烯参与的一锅法连续Stille偶联反应

Scheme 8. One-pot sequential Stille coupling reaction of aryltriazene

图式9. 芳基三氮烯对吲哚C2-位的直接芳基化

Scheme 9. Direct C2 arylation of N-substituted indoles with aryltriazenes

图式10. 芳基三氮烯对芳杂环的直接C—H芳基化

Scheme 10. Direct C—H arylation of heteroarylene with aryltriazene

图式11. 光活化π-共轭三氮烯与非活化芳烃的交叉偶联

Scheme 11. Cross-coupling of π-conjugated triazenes with unactivated arenes via photoactivation

图式12. 钯催化芳基三氮烯和炔烃的Sonogashira插羰反应

Scheme 12. Palladium-catalyzed carbonylative Snogashira coupling between aryl triazenes and alkynes

图式13. 钯催化的芳基三氮烯羰基化反应合成酰胺

Scheme 13. Synthesis of amides by palladium-catalyzed carbonylation of aryltriazenes

图式14. 温和条件下银和钯共催化苯并三唑的羰基化反应合成苯并噁嗪酮

Scheme 14. Silver and palladium co-catalyzed carbonylation of benzotriazoles to synthesis of benzoxazinones under mild conditions

图式15. 铜催化芳基三氮烯为芳基源的胺芳基化反应

Scheme 15. Copper catalyzed N-arylation of amines using aryl triazenes as aryl source

图式16. 通过芳基三氮烯与腈反应合成酰胺

Scheme 16. Synthesis of amide from triazenes and nitrile

图式17. 通过芳基三氮烯合成二芳基硫醚

Scheme 17. Synthesis of diaryl sulfide from aryltriazenes

图式18. 通过磺酰肼与芳基三氮烯合成芳基砜

Scheme 18. Synthesis of aryl sulfone from sulfonyl hydrazine and aryl triazene

图式19. 锌催化芳基三氮烯的硼化反应

Scheme 19. Zn-catalyzed borylation of aryltriazenes

图式20. 通过芳基三氮烯邻位C—H官能团化/分子内环化串联反应合成吲唑化合物

Scheme 20. Synthesis of indazole compounds via aromatic C—H bond carbenoid functionalization/intramolecular cyclization of triazenes

图式21. 离子液体促进的芳基氮杂环与芳基三氮稀的偶氮化反应

Scheme 21. Ionic liquid promoted diazenylation of N-heterocyclic compounds with aryltriazenes

图式22. Brønsted酸性离子液体促进的吡唑酮与芳基三氮烯的直接偶氮化反应

Scheme 22. Brønsted acidic ionic liquid promoted direct diazenylation of pyrazolones with aryltriazenes

图式23. Brønsted酸性离子液体促进萘酚与芳基三氮烯的偶氮化反应

Scheme 23. Brønsted acidic ionic liquid promoted diazenylation of naphthol with aryltriazenes

图式24. 调控芳基三氮烯对吲哚的C2-芳基化和C3-偶氮化

Scheme 24. Controllable C2 arylation and C3 diazenylation of indoles with aryltriazenes

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芳基三氮烯作为芳基前体和芳基偶氮前体在有机合成中的应用研究进展

Research Progress of Aryltriazene as Aryl Precursor and Aryl-Azo Precursors in Organic Synthesis

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