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A One-Pot Construction of Halogenated Trifluoromethylated Pyrroles through NXS (X = Br, I) Triggered Cascade

Chaoqian Huang, Yu Zeng, Huayu Cheng, Anjing Hu, Lu Liu , Yuanjing Xiao* and Junliang Zhang*

*School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, PR China, Email: yjxiaochem.ecnu.edu.cn, jlzhangchem.ecnu.edu.cn

C. Huang, Y. Zeng, H. Cheng, A. Hu, L. Liu, Y. Xiao, J. Zhang, Org. Lett., 2017, 19, 4968-4971.

DOI: 10.1021/acs.orglett.7b02427 (free Supporting Information)



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Abstract

A sequential intermolecular hydroamination reaction of 2-trifluoromethyl-1,3-enynes with aliphatic primary amines under mild reaction conditions followed by a NXS mediated oxidative cyclization of the hydroamination product provides halogenated trifluoromethylated pyrroles. This method offers mild conditions, high efficiency, readily available starting materials, general substrate scope, and synthetic utility of the products.

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Sequential Cross-Coupling for the Construction of Pentasubstituted Pyrroles



Key Words

pyrroles, NIS


ID: J54-Y2017