硫代磷(膦)酸酯的合成研究进展

doi:10.6023/cjoc202104002

摘要/Abstract

硫代磷(膦)酸酯在农药、医药以及有机合成等研究领域具有广泛应用. 重点总结了由P(O)—H化合物出发合成硫代磷(膦)酸酯类化合物的研究方法, 按硫元素的不同来源分类, 对该类反应的研究进展进行综述.

Organophosphorus compounds which contain phosphorus-sulfur bonds have been widely used in the fields of pesticides, pharmaceuticals and organic synthesis. The recent progress of the methods for the synthesis of phosphorothioate and phosphinothioate from P(O)—H reagents are summarized on the basis of different types of sulfur source.

Key words: phosphorothioate, phosphinothioate, P(O)—H compound

引用此文

刘春琪, 王莉贤, 张兴华. 硫代磷(膦)酸酯的合成研究进展[J]. 有机化学, 2021, 41(8): 2964-2973.

Chunqi Liu, Lixian Wang, Xinghua Zhang. Advances in the Synthesis of Phosphorothioate and Phosphinothioate[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2964-2973.

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图/表 10

图1. 硫代磷酸酯在医药、农药方面的应用

Figure 1. Application of phosphorothioate in medicine and pesticides

图式2. Cs2CO3调节的偶联反应

Scheme 2. Cs2CO3 promoted coupling reaction

图式3. KI/TBPB促进硫代膦酸酯化合物的制备

Scheme 3. KI/TBPB promotes the preparation of thiophosphonate compounds

图式 4. DMSO调节的偶联反应

Scheme 4. DMSO promoted coupling reaction

图式5. 光催化交叉偶联反应构建P(O)—S键

Scheme 5. Photocatalytic cross-coupling reaction to construct P(O)—S bond

图式6. P(O)—H与二硫化物的直接偶联

Scheme 6. Direct coupling of P(O)—H to disulfides

图式 7. CsOH催化氢亚磷酸酯与二硫化物的偶联反应

Scheme 7. Coupling reaction of CsOH catalyzed hydrogen phosphite with disulfide

图式8. Cu催化芳基磺酰氯与烷氧基亚磷酸酯偶联制备S-芳基硫代膦酸酯

Scheme 8. Cu-catalyzed coupling of arylsulfonyl chloride with alkoxy phosphite to prepare S-aryl thiophosphonates

图式9. P(O)—H与磺酸直接偶联构建P(O)—S键

Scheme 9. Metal- and oxidant-free P(O)—S bond construction via direct coupling of P(O)—H with sulfinic acids

图式10. Sn催化制备硫(硒)代膦酸酯

Scheme 10. Preparation of sulfur (selenium) phosphonate by Sn catalysis

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