吸电子基取代的N-芳基磺酰腙作为重氮化合物前体的研究进展

doi:10.6023/A21040179

化学学报 ›› 2021, Vol. 79 ›› Issue (9): 1085-1096.DOI: 10.6023/A21040179 上一篇下一篇

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吸电子基取代的N-芳基磺酰腙作为重氮化合物前体的研究进展

王也铭^a^,^*(), 王宏伟^b, 刘兆洪^b^,^*()

a 吉林工程师范技术学院化学与工业生物工程交叉学科研究院长春 130052
b 东北师范大学化学学院长春 130024

投稿日期:2021-04-26 发布日期:2021-09-17
通讯作者: 王也铭, 刘兆洪

作者简介:

王也铭, 副教授, 1983年出生于吉林省白山市. 2006年7月毕业于东北师范大学化学学院应用化学专业, 获得理学学士学位. 2011年6月, 毕业于东北师范大学化学学院有机化学专业, 师从刘群教授, 获得博士学位. 2011年7月, 就职于吉林师范大学化学学院任讲师, 开始独立的课题研究. 2019年9月, 就职于吉林工程技术师范学院化学与工业生物工程交叉学科研究院任副教授. 主要从事过渡金属催化有机合成反应的研究. 目前, 已在《Chem. Commun.》、《Org. Lett.》、《Eur. J. Org. Chem.》、《Tetrahedron Lett.》、《Synthesis》等期刊上公开发表论文20余篇.

王宏伟, 2014年毕业于鞍山师范学院化学系, 同年进入东北师范大学化学学院有机化学专业, 在毕锡和教授课题组进行硕博连读, 主要从事氟烷基磺酰腙反应性研究.

刘兆洪, 博士, 讲师, 2006年6月, 毕业于四川大学华西药学院药学专业, 获得理学学士学位. 2006~2011年凯莱英医药集团从事医药中间体工艺开发工作. 2012~2018年东北师范大学化学学院有机化学专业攻读博士学位, 师从毕锡和教授. 博士毕业后东北师范大学任讲师, 主要从事银催化卡宾化学研究, 目前以第一作者或通讯作者在《Chem》、《Nat. Commun.》《Angew. Chem. Int. Ed.》、《ACS Catal.》、《Chem. Commun.》、《Org. Lett.》等期刊上公开发表论文20余篇.

基金资助:
项目受吉林省科学技术厅(20200801065GH); 中央高校基本科研业务费专项资金(2412020ZD003); 吉林工程技术师范学院博士科研启动经费专项(BSKJ201921)

Research Progress on EWG-Substituted N-Arylsulfonylhydrazones as the Diazo Compound Precursor

Yeming Wang^a(), Hongwei Wang^b, Zhaohong Liu^b()

a Institute of Chemical and Industrial Bioengineering, Jilin Engineering Normal University, Changchun 130052, China
b School of Chemistry, Northeast Normal University, Changchun 130024, China

Received:2021-04-26 Published:2021-09-17
Contact: Yeming Wang, Zhaohong Liu
Supported by:
Department of Science and Technology of Jilin Province(20200801065GH); Fundamental Research Funds for the Central Universities(2412020ZD003); Doctoral Research Initiation Fund Project of Jilin Engineering Normal University(BSKJ201921)

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摘要/Abstract

N-芳基磺酰腙是一类稳定的重氮化合物替代物, 其中, N-对甲基苯磺酰腙研究历史悠久, 在卡宾化学中占据重要地位, 相关的研究报道及综述较多. 近年来, 作为一类更加温和的重氮替代物, 吸电子基取代的N-芳基磺酰腙参与的化学反应发展迅速, 但是相关的研究梳理工作相对缺乏. 因此, 本综述聚焦于吸电子基取代的N-芳基磺酰腙作为重氮化合物替代物在有机合成反应中的研究进展, 重点总结了N-邻硝基苯磺酰腙和N-邻三氟甲基苯磺酰腙参与的偶联、环化、插入、多组分反应和Doyle-Kirmse等反应.

关键词: 重氮化合物, N-邻硝基苯磺酰腙, N-邻三氟甲基苯磺酰腙, N-对甲基苯磺酰腙

N-arylsulfonyl hydrazones were a kind of stable diazo surrogates in organic synthesis. Among them, N-tosylhydrazones occupied main position in the research of carbene chemistry, and many reactions involving N-tosylhydrazones and reviews were published. In recent years, the chemical reactions involving electron-withdrawing groups (EWG)-substituted N-arylsulfonylhydrazones as milder diazo surrogates have been developed rapidly. However, these reactions were not summarized. Therefore, this review focuses on the research progress on EWG-substituted N-arylsulfonylhydrazones used as diazo surrogates in organic synthesis reactions, and emphasized the coupling, cyclization, insertion, multicomponent and Doyle-Kirmse reaction involved N-o-nitrobenzenesulfonylhydrazides and N-o-triftosylhydrazones.

Key words: diazo compound, N-o-nitrobenzenesulfonylhydrazide, N-o-triftosylhydrazone, N-tosylhydrazone

引用此文

王也铭, 王宏伟, 刘兆洪. 吸电子基取代的N-芳基磺酰腙作为重氮化合物前体的研究进展[J]. 化学学报, 2021, 79(9): 1085-1096.

Yeming Wang, Hongwei Wang, Zhaohong Liu. Research Progress on EWG-Substituted N-Arylsulfonylhydrazones as the Diazo Compound Precursor[J]. Acta Chimica Sinica, 2021, 79(9): 1085-1096.

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图/表 28

图1. N-芳基苯磺酰腙原位生成重氮化合物及其应用

Figure 1. Formation of diazocompounds in situ from N-arylsulfonyl- hydrazones and its synthetic applications

图2. 邻硝基策略促进N-芳基苯磺酰肼N―S键断裂

Figure 2. Cleavage of N―S bond of N-arylsulfonylhydrazones promoted by o-nitro group

图3. 磺酰基取代基和温度对N-芳基苯磺酰腙分解的影响

Figure 3. Effect of sulfonyl substitution and temperature on decomposition of N-arylsulfonylhydrazones

图4. 芳香醛衍生的N-芳基磺酰腙与2-氨基-3-溴芳环化合物的反应

Figure 4. Reactions of aromatic aldehyde derivated N-arylsulfonyl- hydrazones with 2-amino-3-bromo-aromatic compounds

图5. 芳香醛衍生的N-芳基磺酰腙与2-溴苯胺的反应

Figure 5. Reactions of aromatic aldehyde derivated N-arylsulfonyl- hydrazones with 2-bromophenylamine

图6. 芳香醛衍生的N-邻硝基苯磺酰腙与α-重氮基酯类、酰胺以及磷酸酯的反应

Figure 6. Reactions of aromatic aldehyde derivated N-o-nitrophenyl- sulfonylhydrazones with α-diazo esters, amides and phosphonates

图7. 炔基醛衍生的N-邻硝基苯磺酰腙与硼酸的反应

Figure 7. Reactions of alkynyl aldehyde derivated N-o-nitrophenyl- sulfonylhydrazones with boronic acids

图8. 芳香醛衍生的N-邻硝基苯磺酰腙与亚硝基芳烃的反应

Figure 8. Reactions of aromatic aldehyde derivated N-o-nitrophenyl- sulfonylhydrazones with nitrosoarenes

图9. 三氟取代乙醛的N-邻三氟甲基苯磺酰腙与RXH (X=O, S, Se, N)的反应

Figure 9. Reactions of RXH (X=O, S, Se, N) with trifluoroacetaldehyde N-o-trifluoro- methylphenylsulfonylhydrazones

图10. 三氟取代乙醛的N-邻三氟甲基苯磺酰腙与有机硼酸的反应

Figure 10. Reactions of trifluoroacetaldehyde N-o-trifluoromethyl- phenylsulfonylhydrazones with organoboronic acids

图11. 芳醛的N-邻三氟甲基苯磺酰腙与异腈的反应

Figure 11. Reactions of aromatic aldehyde N-o-trifluoromethylphenyl- sulfonylhydrazones with isocyanides

图12. 过渡金属催化N-芳基磺酰腙与不饱和烃的反应

Figure 12. Transition metal-catalyzed reactions of N-arylsulfonyl- hydrazones with unsaturated hydrocarbon

图13. 银催化N-邻硝基苯磺酰腙与炔烃的反应

Figure 13. Silver-catalyzed reactions of N-o-nitrophenylsulfonyl- hydrazones with alkynes

图14. 银催化N-邻硝基苯磺酰腙与烯烃的反应

Figure 14. Silver-catalyzed reactions of N-o-nitrophenylsulfonyl- hydrazones with alkenes

图15. 过渡金属催化N-邻硝基苯磺酰腙与烯烃的反应机理

Figure 15. Possible mechanism of transition metals-catalyzed reactions of N-o-nitrophenylsulfonylhydrazones with alkenes

图16. 铁催化N-邻硝基苯磺酰腙与烯烃的反应

Figure 16. Iron-catalyzed reactions of alkenes with N-o-nitrophenyl- sulfonylhydrazones

图17. 三氟取代乙醛的N-邻三氟甲基苯磺酰腙与烯烃的反应

Figure 17. Reactions of trifluoroacetaldehyde N-o-trifluoromethyl- phenylsulfonylhydrazones with alkenes

图18. 二氟取代乙醛的N-芳磺酰腙的制备及其与烯烃的反应

Figure 18. Synthesis of difluoroacetaldehyde N-arylsulfonylhydrazones and reactions with alkenes

图19. 二氟取代乙醛的N-邻三氟甲基苯磺酰腙与烯烃的反应

Figure 19. Reactions of difluoroacetaldehyde N-o-trifluoromethyl- phenylsulfonylhydrazones with alkenes

图20. N-芳基磺酰腙与[60]富勒烯的反应

Figure 20. Reactions of N-arylsulfonylhydrazones with [60]fullerene

图21. N-对甲氧基苯磺酰腙与[60]富勒烯的反应

Figure 21. Reactions of N-p-methoxylsulfonylhydrazones with [60]fullerene

图22. N-芳基磺酰腙与TMSCF3的反应

Figure 22. Reactions of N-arylsulfonylhydrazones with TMSCF3

图23. 三氟取代乙醛的N-邻三氟甲基苯磺酰腙与炔的反应

Figure 23. Reactions of trifluoroacetaldehyde N-o-trifluoromethyl- phenylsulfonylhydrazones with alkynes

图24. 银促进下的N-邻硝基苯磺酰腙对X―H (X=Si, Sn, Ge)键的插入反应

Figure 24. Silver-promoted insertion into X―H (X=Si, Sn, Ge) bonds with N-o-nitrophenylsulfonylhydrazones

图25. N-邻三氟甲基芳磺酰腙与烷烃的反应

Figure 25. Reactions of N-o-trifluoromethylphenylsulfonylhydrazones with alkanes

图26. N-邻三氟甲基芳磺酰腙与烷烃的反应

Figure 26. Reactions of N-o-trifluoromethylphenylsulfonylhydrazones with alkanes

图27. 银介导的N-对硝基苯磺酰腙、[60]富勒烯和腈的三组分反应

Figure 27. Silver-Mediated three-component reaction of N-nitrophenyl- sulfonylhydrazones, [60]fullerene and nitriles

图28. 二氟/三氟取代乙醛的N-邻三氟甲基芳磺酰腙与烯丙基/炔丙基硫醚的反应

Figure 28. Reactions of difluoro/trifluoroacetaldehyde N-o-trifluoro- methylphenylsulfonylhydrazones with allyl/propargyl thioethers

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吸电子基取代的N-芳基磺酰腙作为重氮化合物前体的研究进展

Research Progress on EWG-Substituted N-Arylsulfonylhydrazones as the Diazo Compound Precursor

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