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

doi:10.6023/cjoc202102014

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2587-2600.DOI: 10.6023/cjoc202102014 Previous Articles Next Articles

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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

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)

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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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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Fig. & Tab. 26

Figure 1. Structure and the reaction sites of ayltriazene

Scheme 1. Common synthetic methods of aryltriazene

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

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

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

Scheme 4. Decarboxylative coupling of aryltriazene with cinnamic acid

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

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

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

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

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

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

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

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

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

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

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

Scheme 16. Synthesis of amide from triazenes and nitrile

Scheme 17. Synthesis of diaryl sulfide from aryltriazenes

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

Scheme 19. Zn-catalyzed borylation of aryltriazenes

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

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

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

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

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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