芳香重氮盐参与的协同环加成反应

doi:10.3866/PKU.DXHX202101026

大学化学 >> 2021, Vol. 36 >> Issue (12): 2101026.doi: 10.3866/PKU.DXHX202101026

芳香重氮盐参与的协同环加成反应

彭星, 张发光(), 马军安()

天津大学理学院化学系, 天津 300072

收稿日期:2021-01-13 录用日期:2021-03-03 发布日期:2021-03-29
通讯作者: 张发光,马军安 E-mail:zhangfg1987@tju.edu.cn;majun_an68@tju.edu.cn
作者简介:马军安, Email: majun_an68@tju.edu.cn
张发光, Email: zhangfg1987@tju.edu.cn
基金资助:
国家自然科学基金(21772142);国家自然科学基金(21901181);国家自然科学基金(21961142015)

Aryl Diazonium Salts in Concerted Cycloaddition Reactions

Xing Peng, Fa-Guang Zhang(), Jun-An Ma()

Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China

Received:2021-01-13 Accepted:2021-03-03 Published:2021-03-29
Contact: Fa-Guang Zhang,Jun-An Ma E-mail:zhangfg1987@tju.edu.cn;majun_an68@tju.edu.cn

摘要/Abstract

摘要：

芳香重氮盐由于合成简单及多重反应性，在有机合成中占有重要地位。尽管芳香重氮盐的脱氮气交叉偶联反应、还原反应及与富电子芳烃的偶合反应已得到广泛应用，但是其参与的环加成反应却长期未受重视，在大学化学学习中也无相关介绍。值得注意的是，近年芳香重氮盐参与的成环反应日益增多，也为丰富和发展多样性的含氮杂环化合物提供了一种有效途径。因此，本文概述了芳香重氮盐协同环加成反应的最新进展及其在杂环合成方面的全新应用和机遇。

关键词: 芳香重氮盐, 环加成反应, 四氮唑, 三氮唑

Abstract:

Aryl diazonium salts are a class of important synthons in the field of organic synthesis due to their versatile reactivity and easy availability. Despite the widespread use of the denitrogenation-type cross-coupling, reduction, and azo-coupling reactions of aryl diazonium salts, the cycloaddition reactions of aryl diazonium salts have long been neglected. Noteworthy is that recent renaissance in this type of reactions has open powerful access to a diverse array of N-heterocycles. This minireview summarizes the latest development and applications of cycloaddition reactions of aryl diazonium salts as well as their new opportunity in organic synthesis.

Key words: Aryl diazonium salts, Cycloaddition, Tetrazoles, Triazoles

MSC2000:

彭星, 张发光, 马军安. 芳香重氮盐参与的协同环加成反应[J]. 大学化学, 2021, 36(12): 2101026.

Xing Peng, Fa-Guang Zhang, Jun-An Ma. Aryl Diazonium Salts in Concerted Cycloaddition Reactions[J]. University Chemistry, 2021, 36(12): 2101026.

图/表 4

参考文献 33

1	Gall C. Chem. Rev. 1988, 88, 765. doi: 10.1021/cr00087a004
2	Griess J. P. Justus Liebigs Ann. Chem. 1858, 106, 123. doi: 10.1002/jlac.18581060114
3	Oger N. ; d'Halluin M. ; Le Grognec E. ; Felpin F.-X. Org. Process Res. Dev. 2014, 18, 1786. doi: 10.1021/op500299t
4	Mo F. ; Dong G. ; Zhang Y. ; Wang J. Org. Biomol. Chem. 2013, 11, 1582. doi: 10.1039/c3ob27366k
5	Mo F. ; Qiu D. ; Zhang Y. ; Wang J. Acc. Chem. Res. 2018, 51, 496. doi: 10.1021/acs.accounts.7b00566
6	Gomberg M. ; Bachmann W. E. J. Am. Chem. Soc. 1924, 46, 2339. doi: 10.1021/ja01675a026
7	Balz G. ; Schiemann G. Ber. Dtsch. Chem. Ges. 1927, 60, 1186. doi: 10.1002/cber.19270600539
8	Hari D. P. ; König B. Angew. Chem. Int. Ed. 2013, 52, 4734. doi: 10.1002/anie.201210276
9	Roglans A. ; PlaQuintana A. ; Moreno-Mañas M. Chem. Rev. 2006, 106, 4622. doi: 10.1021/cr0509861
10	Merino E. Chem. Soc. Rev. 2011, 40, 3835. doi: 10.1039/c0cs00183j
11	邢其毅; 裴伟伟; 徐瑞秋; 裴坚. 基础有机化学, 第4版北京: 北京大学出版社.
12	Zhang F.-G. ; Chen Z. ; Cheung C.-W. ; Ma J.-A. Chin. J. Chem. 2020, 38, 1132. doi: 10.1002/cjoc.202000270
13	Meyer K. H. Ber. Dtsch. Ges. 1919, 52, 1468. doi: 10.1002/cber.19190520809
14	Sheppard W. A. ; Webster O. W. J. Am. Chem. Soc. 1973, 95, 2695. doi: 10.1021/ja00789a054
15	Carlson B. A. ; Sheppard W. A. ; Webster O. W. J. Am. Chem. Soc. 1975, 97, 5291. doi: 10.1021/ja00851a052
16	Bronberger F. ; Huisgen R. Tetrahedron Lett. 1984, 25, 57. doi: 10.1016/S0040-4039(01)91147-5
17	Neochoritis C. G. ; Zhao T. ; Dömling A. Chem. Rev. 2019, 119, 1970. doi: 10.1021/acs.chemrev.8b00564
18	Demko Z. P. ; Sharpless K. B. Angew. Chem. Int. Ed. 2002, 41, 2110. doi: 10.1002/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO;2-7
19	Huisgen R. Angew. Chem. Int. Ed. 1963, 2, 565. doi: 10.1002/anie.196305651
20	Breugst M. ; Reissig H.-U. Angew. Chem. Int. Ed. 2020, 59, 12293. doi: 10.1002/anie.202003115
21	Liang L. ; Astruc D. Coord. Chem. Rev. 2011, 255, 2933. doi: 10.1016/j.ccr.2011.06.028
22	Huisgen R. ; Koch H.-J. Liebigs Ann. Chem. 1955, 591, 200. doi: 10.1002/jlac.19555910206
23	Chen Z. ; Fan S.-Q. ; Zheng Y. ; Ma J.-A. Chem. Commun. 2015, 51, 16545. doi: 10.1039/C5CC07324C
24	Peng X. ; Xiao M.-Y. ; Zeng J.-L. ; Zhang F.-G. ; Ma J.-A. Org. Lett. 2019, 21, 4808. doi: 10.1021/acs.orglett.9b01697
25	Zhai S.-J. ; Peng X. ; Zhang F.-G. ; Ma J.-A. Org. Lett. 2019, 21, 9884. doi: 10.1021/acs.orglett.9b03800
26	Xiao M.-Y. ; Chen Z. ; Zhang F.-G. ; Ma J.-A. Tetrahedron 2020, 76, 131063. doi: 10.1016/j.tet.2020.131063
27	Liu X.-Y. ; Zhai S.-J. ; Feng F.-F. ; Zhang F.-G. ; Ma J.-A. ChemCatChem 2020, 12, 5623. doi: 10.1002/cctc.202001143
28	Xiao M.-Y. ; Zheng M.-M. ; Peng X. ; Xue X.-S. ; Zhang F.-G. ; Ma J.-A. Org. Lett. 2020, 22, 7762. doi: 10.1021/acs.orglett.0c03025
29	Zhang F.-G. ; Peng X. ; Ma J.-A. Chin. J. Org. Chem. 2019, 39, 109. doi: 10.6023/cjoc201808007
30	Li H. ; Wu X. ; Hao W. ; Li H. ; Zhao Y. ; Wang Y. ; Lian P. ; Zheng Y. ; Bao X. ; Wan X. Org. Lett. 2018, 20, 5224. doi: 10.1021/acs.orglett.8b02172
31	Peng X. ; Zhang F.-G. ; Ma J.-A. Adv. Synth. Catal. 2020, 362, 4432. doi: 10.1002/adsc.202000776
32	Zhou L.-N. ; Feng F.-F. ; Cheung C.-W. ; Ma J.-A. Org. Lett. 2021, 23, 739. doi: 10.1021/acs.orglett.0c03960
33	Yu X.-Y. ; Xiao W.-J. ; Chen J.-R. Eur. J. Org. Chem. 2019, 6994.

芳香重氮盐参与的协同环加成反应

Aryl Diazonium Salts in Concerted Cycloaddition Reactions

RichHTML

PDF (PC)

赞

可视化

摘要/Abstract

引用本文

使用本文

图/表 4

参考文献 33

相关文章 1

Metrics

推荐阅读 0