Catalyst-Free Synthesis of Phosphorothioates via P-S Coupling -Reaction of Dialkyl Phosphites with Thiols

被引：0

作者：

Kaboudin, Babak ^{[1
]}

Daliri, Payam ^{[1
]}

Esfandiari, Hesam ^{[1
]}

Kazemi, Foad ^{[1
]}

机构：

[1] Inst Adv Studies Basic Sci IASBS, Dept Chem, Zanjan 4513766731, Iran

来源：

SYNLETT | 2023年 / 34卷 / 03期

关键词：

phosphorothioates; thiols; H-dialkyl phosphites; coupling reaction; catalyst-free; ARYL PHOSPHOROTHIOATES; BIOLOGICAL EVALUATION; PHOSPHONATES; DERIVATIVES; PHOSPHORUS; ACIDS;

D O I：

10.1055/a-1983-1640

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst-free synthesis of phosphorothioates via a P-S cross-coupling reaction of thiols with dialkyl phosphites has been studied. With presented method, various phosphorothioates were obtained by the reaction of thiols with H-dialkyl phosphites in the presence of DMSO as both solvent and oxidant under transition-metal-free conditions. Mechanistic studies showed that the reaction proceeds with formation of a known disulfide intermediate via the oxidation of thiols in the presence of DMSO. Nucleophilic substitution of dialkyl phosphite with the disulfide intermediate gave phosphorothioate. The presented method is a convenient process for the synthesis of phosphorothioates under catalyst-free conditions.

引用

页码：249 / 252

页数：4

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