Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp²)-H or C(sp)-H Bond

Yuxing Fan, Yongqin He, Xingxing Liu, Ting Hu, Haojie Ma, Xiaodong Yang, Xinliang Luo and Guosheng Huang*

*State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, 730000, P. R. China, Email: hgslzu.edu.cn

Y. Fan, Y. He, X. Liu, T. Hu, H. Ma, X. Yang, X. Luo, G. Huang, J. Org. Chem., 2016, 81, 6820-6825.

DOI: 10.1021/acs.joc.6b01135

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Abstract

I₂ promotes a metal-free domino protocol for the one-pot synthesis of 1,3,4-oxadiazoles in good yields via oxidative cleavage of C(sp²)-H or C(sp)-H bonds, followed by cyclization and deacylation. The use of K₂CO₃ is an essential factor in the cyclization and the C-C bond cleavage. This procedure offers good functional group compatibility.

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Key Words

1,3,4-oxadiazoles, oxygen, iodine

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ID: J42-Y2016