Cesium-Catalyzed Regioselective Synthesis of Trisubstituted Heteroatom Alkenes: A New Strategy for the Preparation of Functional Alkenes

被引：25

作者：

Chen, Jinyang ^{[1
]}

Tang, Zhi ^{[1
]}

Qiu, Renhua ^{[1
]}

He, Yunhua ^{[1
]}

Wang, Xie ^{[1
]}

Li, Ningbo ^{[1
]}

Yi, Haibo ^{[1
]}

Au, Chak-Tong ^{[1
]}

Yin, Shuang-Feng ^{[1
]}

Xu, Xinhua ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemobiosensing & Chemometr, Changsha 410082, Hunan, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 09期

基金：

中国国家自然科学基金;

关键词：

HIGHLY SELECTIVE THIOSELENATION; CARBON TETRASUBSTITUTED ALKENES; SELENIUM STABILIZED CARBANIONS; STEREOSELECTIVE-SYNTHESIS; VINYLIC TELLURIDES; OLEFINS; REAGENTS; SULFONES; TAMOXIFEN; ALKYNES;

D O I：

10.1021/acs.orglett.5b00751

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly chemo-, regio-, and stereoselective method for the synthesis of (Z)-vinylic selenosulfides and (Z)-vinylic tellurosulfides in a one-pot reaction of terminal alkynes, diaryl disulfides, and diaryl diselenides (ditellurides) catalyzed by simple base cesium hydroxide monohydrate is described. Due to the different activities of the carbon-chalcogen bonds, the target products cleave selectively and act as a kind of readily available platform molecule for the synthesis of tetrasubstituted alkenes. The mechanism of thioselenation was studied by experimental and theoretical methods.

引用

页码：2162 / 2165

页数：4

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