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

doi:10.6023/A21040179

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (9): 1085-1096.DOI: 10.6023/A21040179 Previous Articles Next Articles

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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)

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

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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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Fig. & Tab. 28

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Figure 22. Reactions of N-arylsulfonylhydrazones with TMSCF3

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

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

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

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

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

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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