芳香重氮盐参与的协同环加成反应

doi:10.3866/PKU.DXHX202101026

Abstract

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:

Xing Peng, Fa-Guang Zhang, Jun-An Ma. Aryl Diazonium Salts in Concerted Cycloaddition Reactions[J].University Chemistry, 0, (): 2101026.

References

[1] Gall, C. Chem. Rev. 1988, 88, 765.
[2] Griess, J. P. Justus Liebigs Ann. Chem. 1858, 106, 123.
[3] Oger, N.; d'Halluin, M.; Le Grognec, E.; Felpin, F.-X. Org. Process Res. Dev. 2014, 18, 1786.
[4] Mo, F.; Dong, G.; Zhang, Y.; Wang, J. Org. Biomol. Chem. 2013, 11, 1582.
[5] Mo, F.; Qiu, D.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2018, 51, 496.
[6] Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1924, 46, 2339.
[7] Balz, G.; Schiemann, G. Ber. Dtsch. Chem. Ges. 1927, 60, 1186.
[8] Hari, D. P.; König, B. Angew. Chem. Int. Ed. 2013, 52, 4734.
[9] Roglans, A.; PlaQuintana, A.; Moreno-Mañas, M. Chem. Rev. 2006, 106, 4622.
[10] Merino, E. Chem. Soc. Rev. 2011, 40, 3835.
[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, 2016.
[12] Zhang, F.-G.; Chen, Z.; Cheung, C.-W.; Ma, J.-A. Chin. J. Chem. 2020, 38, 1132.
[13] Meyer, K. H. Ber. Dtsch. Ges. 1919, 52, 1468.
[14] Sheppard, W. A.; Webster, O. W. J. Am. Chem. Soc. 1973, 95, 2695.
[15] Carlson, B. A.; Sheppard, W. A.; Webster, O. W. J. Am. Chem. Soc. 1975, 97, 5291.
[16] Bronberger, F.; Huisgen, R. Tetrahedron Lett. 1984, 25, 57.
[17] Neochoritis, C. G.; Zhao, T.; Dömling, A. Chem. Rev. 2019, 119, 1970.
[18] Demko, Z. P.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2110.
[19] Huisgen, R. Angew. Chem. Int. Ed. 1963, 2, 565.
[20] Breugst, M.; Reissig, H.-U. Angew. Chem. Int. Ed. 2020, 59, 12293.
[21] Liang, L.; Astruc, D. Coord. Chem. Rev. 2011, 255, 2933.
[22] Huisgen, R.; Koch, H.-J. Liebigs Ann. Chem. 1955, 591, 200.
[23] Chen, Z.; Fan, S.-Q.; Zheng, Y.; Ma, J.-A. Chem. Commun. 2015, 51, 16545.
[24] Peng, X.; Xiao, M.-Y.; Zeng, J.-L.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2019, 21, 4808.
[25] Zhai, S.-J.; Peng, X.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2019, 21, 9884.
[26] Xiao, M.-Y.; Chen, Z.; Zhang, F.-G.; Ma, J.-A. Tetrahedron 2020, 76, 131063.
[27] Liu, X.-Y.; Zhai, S.-J.; Feng, F.-F.; Zhang, F.-G.; Ma, J.-A. ChemCatChem 2020, 12, 5623
[28] Xiao, M.-Y.; Zheng, M.-M.; Peng, X.; Xue, X.-S.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2020, 22, 7762.
[29] Zhang, F.-G.; Peng, X.; Ma, J.-A. Chin. J. Org. Chem. 2019, 39, 109.
[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.
[31] Peng, X.; Zhang, F.-G.; Ma, J.-A. Adv. Synth. Catal. 2020, 362, 4432.
[32] Zhou, L.-N.; Feng, F.-F.; Cheung, C.-W.; Ma, J.-A. Org. Lett. 2021, 23, 739.
[33] Yu, X.-Y.; Xiao, W.-J.; Chen, J.-R. Eur. J. Org. Chem. 2019, 6994.

Aryl Diazonium Salts in Concerted Cycloaddition Reactions

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 10

[1]	Mei Pan, Chaojie Li, Yajun Hou, Chengyong Su. Synthesis and Physical Chemistry Property Study of a Fe(II)-Pd(II) Heteronuclear Metal-Organic Cag: A New Comprehensive Chemistry Experiment [J]. University Chemistry, 0, (): 8-0.
[2]	Jiao Li, Gu Jin, Lingling Li, Qizhi Yao, Hongyu Liu, Xiaokui Wang. Exploration and Practice of the Evaluation Methods for Designing Analytical Chemistry Experiment [J]. University Chemistry, 0, (): 9-0.
[3]	Yun Tian, Xiaofei Ma, Yalu Ma, Xue Qin. Exploration and Practice on Online Final Examinations of Inorganic Chemistry and Chemical Analysis Course [J]. University Chemistry, 0, (): 4-0.
[4]	Junxia Yu, Ruyi Zhou, Ruan Chi. A Comprehensive Chemistry Experiment on the Adsorption of Phosphate by Ferrihydrite Loaded Sugarcane Bagasse [J]. University Chemistry, 0, (): 2-0.
[5]	Man He, Beibei Chen, Bin Hu. Deepen the Understanding of “Distribution Fraction” with Separation/Enrichment of Arsenic Species as Examples [J]. University Chemistry, 0, (): 1-0.
[6]	Jun Li, Ling Zhang, Dan Li, Zhong Cao, Ping Chen, Jinglin He. Practice and Thinking of “XXT Full Online” Teaching Model in Analytical Chemistry Course [J]. University Chemistry, 0, (): 0-0.
[7]	Mingyu Yang. Progress in Synthesis of Pyrrolidine Derivatives by Hofmann-Löffler-Freytag Type Reactions [J]. University Chemistry, 0, (): 1-0.
[8]	Mingyu He, Ying Li, Mamatjan Yimit. The Extraction of Lignin from Cotton Stalks and the Comprehensive Experiment of the Study on the Antioxidant Properties of Polypropylene [J]. University Chemistry, 0, (): 0-0.
[9]	Yuqing Chen, Shaohua Zhuo, Yinuo Ning. Construction of Online Service Platform for Chemical Biology Laboratory [J]. University Chemistry, 0, (): 2-0.
[10]	Houjin Li, Jinshan Li, Liuping Chen. Hydrogen Peroxide: Small Molecule with Big Functions [J]. University Chemistry, 0, (): 3-0.
[11]	Lingling Feng, Qiong Chen, Yumeng Li, Jinghan Liang, Zhou Wang. Preparation of an Important Enzyme FBP/SBPase from Cyanobacteria and Analysis of Interaction between Target Enzyme and Ligand: One Comprehensive Experiment Based on Research [J]. University Chemistry, 0, (): 0-0.
[12]	Jing Chang, Chuang Shang, Wentao Zhao. Experiment Improvement of “Determination of Copper by Constant Current Electrolysis Method” [J]. University Chemistry, 0, (): 1-0.
[13]	Shuzhe Sun, Zehao Zhang, Bin Zhang. Mathematical Interpretation of Initial Curve of Acid-Base Titration between Strong Base and Weak Acid: Taking NaOH and HAc as an Example [J]. University Chemistry, 0, (): 3-0.
[14]	Jiayi Wang, Jiaxi Xu. Theoretical Rationale and Experimental Evidences on Regioselective Rule in Aromatic Electrophilic Substitution of Disubstituted Benzenes [J]. University Chemistry, 0, (): 0-0.
[15]	Xin Hu, Fuling Yin, Jun Yang, Ming Zhao. Determination of Alkali Hydroxide Concentration Based on Green Consideration [J]. University Chemistry, 0, (): 0-0.