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Iron Halide-Mediated Regio- and Stereoselective Halosulfonylation of Terminal Alkynes with Sulfonylhydrazides: Synthesis of (E)-β-Chloro and Bromo Vinylsulfones

Xiaoqing Li*, Xinhua Shi, Mingwu Fang and Xiangsheng Xu*

*College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People’s Republic of China, Email: xqlizjut.edu.cn, futurezjut.edu.cn

X. Li, X. Shi, M. Fang, X. Xu, J. Org. Chem., 2013, 78, 9499-9504.

DOI: 10.1021/jo401581n (free Supporting Information)


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Abstract

Halosulfonylation of terminal alkynes was achieved with sulfonylhydrazides as the sulfonyl precursor and inexpensive iron halide as halide source in the presence of TBHP to yield (E)-β-chloro and bromo vinylsulfones regio- and stereoselectively.

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Key Words

Chlorination, Sulfonylation, TBHP


ID: J42-Y2013