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钯催化末端炔烃的双硫醇化反应以合成多种()-1,2-双(芳硫基)烯烃衍生物。

Palladium-catalyzed bisthiolation of terminal alkynes for the assembly of diverse ()-1,2-bis(arylthio)alkene derivatives.

作者信息

Lai Yin-Long, Yan Shaoxi, He Dan, Zhou Li-Zhen, Chen Zi-Shen, Du Yu-Long, Li Jianxiao

机构信息

College of Chemistry and Civil Engineering, Shaoguan University Shaoguan 512005 P. R. China

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology Guangzhou 510640 P. R. China

出版信息

RSC Adv. 2021 Aug 23;11(46):28447-28451. doi: 10.1039/d1ra05773a.

Abstract

An efficient and straightforward palladium-catalyzed three-component cascade bisthiolation of terminal alkynes and arylhydrazines with sodium thiosulfate (NaSO) as the sulfur source for the assembly of functionalized ()-1,2-bis(arylthio)alkene derivatives is described. Using 0.5 mol% IPr-Pd-Im-Cl as the catalyst, a wide range of terminal alkynes and arylhydrazines are well tolerated, thus producing the desired products in good yields with good functional group tolerance and excellent regioselectivity. Moreover, this protocol could be readily scaled up, showing potential applications in organic synthesis and material science.

摘要

描述了一种高效且直接的钯催化的末端炔烃、芳基肼与硫代硫酸钠(NaSO)的三组分串联双硫醇化反应,该反应以硫代硫酸钠为硫源用于组装官能化的()-1,2-双(芳硫基)烯烃衍生物。使用0.5 mol%的IPr-Pd-Im-Cl作为催化剂,多种末端炔烃和芳基肼都具有良好的耐受性,从而以良好的产率、良好的官能团耐受性和优异的区域选择性得到所需产物。此外,该方法可以很容易地放大规模,在有机合成和材料科学中显示出潜在的应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/31ef/9037987/5cae75b13c8a/d1ra05773a-s1.jpg

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