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

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

Jinyang Chen, Zhi Tang, Renhua Qiu, Yunhua He, Xie Wang, Ningbo Li, Haibo Yi, Chak-Tong Au, Shuang-Feng Yin, Xinhua Xu

Org Lett. 2015 May 1;17(9):2162-5.

PMID: 25885546

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP35103798	Cesium hydroxide monohydrate		35103-79-8	Price

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