氮自由基启动的1,n-烯炔环化反应

doi:10.1016/S1872-2067(20)63702-0

催化学报 ›› 2021, Vol. 42 ›› Issue (5): 731-742.DOI: 10.1016/S1872-2067(20)63702-0

氮自由基启动的1,n-烯炔环化反应

魏文廷^a^,^*(), 李强^a^,^b, 张明忠^c, 何卫民^d^,^#()

^a宁波大学材料科学与化学工程学院, 新型功能材料与制备科学国家重点实验室培育基地, 浙江宁波315211
^b聊城大学化学化工学院, 功能有机分子和材料研究所, 山东聊城252059
^c长江师范学院化学化工学院, 重庆408100
^d长沙理工大学电力与交通材料保护湖南省重点实验室, 湖南长沙410114

收稿日期:2020-06-12 接受日期:2020-06-12 出版日期:2021-05-18 发布日期:2021-01-29
通讯作者: 魏文廷,何卫民
基金资助:
国家自然科学基金(21801142);国家自然科学基金(21802062);浙江省省属高校基本科研业务费专项资金(SJLY2021004);湖南省自然科学基金(2019JJ20008)

N-Radical enabled cyclization of 1,n-enynes

Wen-Ting Wei^a^,^*(), Qiang Li^a^,^b, Ming-Zhong Zhang^c, Wei-Min He^d^,^#()

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, Zhejiang, China
^bInstitution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, Shandong, China
^cSchool of Chemistry and Chemical Engineering, Yangtze Normal University, Chongqing 408100, China
^dHunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science and Technology, Changsha 410114, Hunan, China

Received:2020-06-12 Accepted:2020-06-12 Online:2021-05-18 Published:2021-01-29
Contact: Wen-Ting Wei,Wei-Min He
About author:^# E-mail: weiminhe2016@yeah.net
^* E-mail: weiwenting@nbu.edu.cn;
Supported by:
National Natural Science Foundation of China(21801142);National Natural Science Foundation of China(21802062);Fundamental Research Funds for the Provincial Universities of Zhejiang(SJLY2021004);Hunan Provincial Natural Science Foundation of China(2019JJ20008)

摘要/Abstract

摘要：

C-N键广泛存在于药物、天然产物和功能材料中, 而氮中心自由基在C-N键的构建中起到关键作用. 但是, 与广泛使用的碳中心自由基相比, 氮中心自由基由于缺乏实用简便的产生方法而尚未得到充分研究. 因此, 发展高效的氮中心自由基引发反应迫在眉睫. 在过去的几年里, 得益于可信赖且可控制的自由基化学的兴起, 可以通过热分解、氧化剂促进、金属盐催化或电催化来产生氮中心自由基.

1,n-烯炔环化不仅可以一步反应同时构建形成两个或多个新的化学键, 而且可以高选择性引入各种外部官能团, 被认为是构建复杂环状化合物必不可少的方法. 传统上, 通过贵金属(例如Au、Pd、Rh、Ru等)和/或引发剂介导/催化来实现1,n-烯炔环化反应. 1985年, Curran和他的同事报道了具有里程碑意义的工作, 该方法通过碘代烯炔类化合物的分子内自由基串联环化反应实现了(±)-hirsutene的简洁全合成. 受该工作的启发, 并伴随着现代合成技术的发展, 自由基启动的1,n-烯炔环化由于反应条件温和、具有较高的官能团兼容性、原子利用率高、通常不使用化学计量的金属催化剂和/或有毒引发剂, 因而受到化学家们越来越多的关注.

在此背景下, 化学工作者已经开发了多种氮中心自由基启动的1,n-烯炔类化合物环化反应的方法. 然而, 据我们所知, 目前还没有专门针对该主题的综述, 因此本文及时进行总结分析. 迄今为止, 氮中心自由基启动的1,n-烯炔环化反应大概分为三种途径: (1)氮中心自由基选择性的与1,n-烯炔的C=C键进行加成反应, 然后通过分子内环化以生成烯基自由基中间体, 最后借助进一步环化反应、氢原子攫取或自由基偶联以得到最终产物; (2)涉及到氮中心自由基与1,n-烯炔的C≡C键的选择性加成反应、分子内环化及氧化脱氢; (3)借助分子内原位生成的氮中心自由基来启动的, 随后经过两次分子内环化、单电子转移氧化及脱氢反应转化为最终产物. 本文将依据氮中心自由基的类型, 分为硝基自由基、叠氮自由基和酰胺自由基进行讨论, 并将重点放在生成氮中心自由基的方法及其环化模式、相关反应机理以及存在的挑战上.

关键词: 1,n-烯炔, 氮自由基, 环化, C-N键

Abstract:

Compared to the widely used carbon-centered radicals, N-radicals have been relatively unexplored owing to the lack of practical and convenient production methods. Over the past few years, benefitting from the resurgence of reliable and controllable radical chemistry, N-radicals have been produced via thermal decomposition, oxidants, metal salts, or electrocatalysis. Therefore, numerous N-radical enabled cyclization of 1,n-enynes methods have been developed, providing a versatile and concise synthetic platform for the preparation of complex cyclic systems and natural products containing elaborate ring frameworks. In this review, we will summarize recent advances in the promising field of radical chemistry focusing on the production methods of N-radicals and their cyclization patterns, associated mechanisms, unmet challenges, and future opportunities.

Key words: 1,n-Enynes, N-Radical, Cyclization, C-N bond

魏文廷, 李强, 张明忠, 何卫民. 氮自由基启动的1,n-烯炔环化反应[J]. 催化学报, 2021, 42(5): 731-742.

Wen-Ting Wei, Qiang Li, Ming-Zhong Zhang, Wei-Min He. N-Radical enabled cyclization of 1,n-enynes[J]. Chinese Journal of Catalysis, 2021, 42(5): 731-742.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(20)63702-0

https://www.cjcatal.com/CN/Y2021/V42/I5/731

图/表 50

Scheme 1. Intramolecular radical cascade cyclization of iodo-enyne.

Scheme 2. Overview of N-radical enabled cyclization of 1,n-enynes.

Scheme 3. Generation of NO2 radical and its chemoselectivity addition to 1,n-enynes.

Scheme 4. Cascade nitration/cyclization of 1,7-enynes for the synthesis of pyrrolo[4,3,2-de]quinolinones.

Scheme 5. 18O-Labeled experiment and suggested mechanism for cascade nitration/cyclization of 1,7-enynes.

Scheme 6. Nitrative cyclization of 1-ethynyl-2-(vinyloxy)benzenes.

Scheme 7. 18O-Labeled experiments and suggested mechanism for nitrative cyclization of 1-ethynyl-2-(vinyloxy)benzenes.

Scheme 8. Nitro-carbocyclization of 1,6-enynes.

Scheme 9. Suggested mechanism for nitro-carbocyclization of 1,6-enynes.

Scheme 10. Regioselective nitrative cyclization of 1,6-enynes.

Scheme 11. Control experiments and suggested mechanism for regioselective nitrative cyclization of 1,6-enynes.

Scheme 12. Cu(NO3)2/oxone-mediated nitration cyclization of 1,6-enynes.

Scheme 13. Generation of N3 radical and azidation of 1,n-enynes.

Scheme 14. Copper catalyzed [2+2+1] annulation of 1,n-enynes.

Scheme 15. Suggested mechanism for copper catalyzed [2+2+1] annulation of 1,n-enynes.

Scheme 16. Transition-metal controlled diastereodivergent azidation of 1,7-enynes.

Scheme 17. Suggested model for Mn- and Cu-controlled diastereodivergence.

Scheme 18. Azidation/cyclization of 1,6-enynes with N3 sources.

Scheme 19. Control experiments and suggested mechanism for azidation/cyclization of 1,6-enynes with N3 sources.

Scheme 20. Haloazidation of 1,7-enynes for the construction of 3,4-dihydroquinolin-2(1H)ones.

Scheme 21. Suggested mechanism for haloazidation of 1,7-enynes.

Scheme 22. Haloazidation of 1,6-enynes for the synthesis of 2-pyrrolidinones.

Scheme 23. Iodoazidation of para-quinone methides.

Scheme 24. Haloazidation of 1,6-enynes for the synthesis of succinimide derivatives.

Scheme 25. Electrochemical dehydrogenative cyclization of arylamine-tethered 1,5-enynes.

Scheme 26. Suggested mechanism for electrochemical dehydrogenative cyclization of arylamine-tethered 1,5-enynes.

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氮自由基启动的1,n-烯炔环化反应

N-Radical enabled cyclization of 1,n-enynes

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