Copper(II)-Catalyzed Chemo- and Stereocontrolled Synthesis of (E)-Vinyl Sulfones and (Z)-β-Chlorovinyl Sulfones from Terminal Alkynes and Arylsulfonyl Hydrazides

Xiao-Tao Liu; Zong-Cang Ding; Lu-Chuan Ju; Su-Xia Xu; Zhuang-Ping Zhan

doi:10.1055/s-0036-1588918

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(07): 1575-1582
DOI: 10.1055/s-0036-1588918

paper

Copper(II)-Catalyzed Chemo- and Stereocontrolled Synthesis of (E)-Vinyl Sulfones and (Z)-β-Chlorovinyl Sulfones from Terminal Alkynes and Arylsulfonyl Hydrazides

Xiao-Tao Liu*

^aHuaian Wanbang Aromatic Chemicals Industry Co., Ltd. Huaian, Jiangsu, P. R. of China eMail: Xiaotao.Liu@wxintl.com

,

Zong-Cang Ding

^bDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China eMail: zpzhan@xmu.edu.cn

,

Lu-Chuan Ju

^bDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China eMail: zpzhan@xmu.edu.cn

,

Su-Xia Xu

^bDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China eMail: zpzhan@xmu.edu.cn

,

Zhuang-Ping Zhan*

^bDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China eMail: zpzhan@xmu.edu.cn

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Abstract

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Abstract

A facile copper(II)-catalyzed regio- and stereocontrolled synthesis of vinyl sulfones from terminal alkynes and arylsulfonyl hydrazides is described. Depending on the source of copper(II), two different kinds of vinyl sulfones, (E)-vinyl sulfones and (Z)-β-chlorovinyl sulfones were obtained and the addition of cyclohexanone played an important role in the reaction. These reactions display excellent chemoselectivity as well as stereoselectivity.

Key words

copper(II) - catalysis - vinyl sulfones - terminal alkynes - arylsulfonyl hydrazides - cyclohexanone - chemoselectivity - stereoselectivity

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Referenzen

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