Catalyst-Free Synthesis of Phosphorothioates via P–S Coupling Reaction of Dialkyl Phosphites with Thiols
| Autor: | Babak Kaboudin, Payam Daliri, Hesam Esfandiari, Foad Kazemi |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Synlett. 34:249-252 |
| ISSN: | 1437-2096 0936-5214 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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