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Iron-Mediated Synthesis of Isoxazoles from Alkynes: Using Iron(III) Nitrate as a Nitration and Cyclization Reagent

Zhenzhen Lai, Zhenxing Li, Yawei Liu, Pengkun Yang, Xiaomin Fang, Wenkai Zhang, Baoying Liu, Haibo Chang, Hao Xu* and Yuanqing Xu*

*College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China, Email:,

Z. Lai, Z. Li, Y. Liu, P. Yang, X. Fang, W. Zhang, B. Liu, H. Chang, H. Xu, Y. Xu, J. Org. Chem., 2018, 83, 145-153.

DOI: 10.1021/acs.joc.7b02483

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Using cheap and eco-friendly iron(III) nitrate as the nitration and cyclization reagent and KI as an additive for the synthesis of isoxazoles from alkynes, both self-coupling and cross-coupling products could be successfully prepared. In the cross-coupling and cyclizing of two different alkynes, the iron-mediated system shows a good chemoselectivity.

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proposed mechanism

Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-oxadiazoles from Alkynes and Nitriles: The Dual Roles of Iron Nitrate

Q. Bian, C. Wu, J. Yuan, Z. Shi, T. Ding, Y. Huang, H. Xu, Y. Xu, J. Org. Chem., 2020, 85, 4058-4066.

Key Words

Isoxazoles, Multicomponent Reactions

ID: J42-Y2018