Direct Synthesis of 4-Aryl-1,2,3-triazoles via I₂-Promoted Cyclization under Metal- and Azide-Free Conditions

Chun Huang, Xiao Geng, Peng Zhao, You Zhou, Xiao-Xiao Yu, Li-Sheng Wang, Yan-Dong Wu and An-Xin Wu*

*Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, P. R. China, Email: chwuaxmail.ccnu.edu.cn

C. Huang, X. Geng, P. Zhao, Y. Zhou, X.-X. Yu, L.-S. Wang, Y.-D. Wu, A.-X. Wu, J. Org. Chem., 2021, 86, 13664-13672.

DOI: 10.1021/acs.joc.1c01702

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Abstract

An iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide provides 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. This is achieved using p-toluenesulfonyl hydrazines and 1-aminopyridinium iodide as azide surrogates.

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proposed mechanism

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Key Words

1,2,3-triazoles, multicomponent reactions, iodine

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ID: J42-Y2021