光/电化学驱动硫代磷酸酯类化合物的合成研究进展

doi:10.6023/cjoc202410018

有机化学 ›› 2025, Vol. 45 ›› Issue (10): 3719-3740.DOI: 10.6023/cjoc202410018 上一篇下一篇

综述与进展

光/电化学驱动硫代磷酸酯类化合物的合成研究进展

郭国菊^a, 吴启龙^a, 董宇振^a, 张洁^c, 石永佳^a, 柳清^a^,^b^,^*(), 杨道山^a^,^d^,^*()

^a 青岛科技大学化学与分子工程学院山东青岛 266042
^b 河北民族师范学院化学与化工学院河北承德 067000
^c 青岛科技大学高分子科学与工程学院山东青岛 266042
^d 南京林业大学林木生物质低碳高效利用国家工程研究中心南京 210037

收稿日期:2024-10-25 修回日期:2024-11-27 发布日期:2025-01-03
基金资助:
国家自然科学基金(22271170); 山东省泰山专家项目(tsqn202408197); 山东省自然科学基金(ZR2024QB154)

Research Progress in the Synthesis of Phosphorothioates Driven by Photo/Electrochemistry

Guoju Guo^a, Qilong Wu^a, Yuzhen Dong^a, Jie Zhang^c, Yongjia Shi^a, Qing Liu^a^,^b^,^*(), Daoshan Yang^a^,^d^,^*()

^a College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao,Shandong 266042
^b College of Chemistry and Chemical Engineering, Hebei Minzu Normal University, Chengde, Hebei 067000
^c School of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
^d National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037

Received:2024-10-25 Revised:2024-11-27 Published:2025-01-03
Contact: * yangdaoshan@tsinghua.org.cn; chemistryliu@163.com
Supported by:
National Natural Science Foundation of China(22271170); Taishan Scholars Program from Shandong Province(tsqn202408197); Natural Science Foundation of Shandong Province(ZR2024QB154)

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摘要/Abstract

硫代磷酸酯类化合物是一类含有S—P(O)键的有机磷化物, 具有重要的化学和生物学特性, 广泛应用于有机合成、药物化学和农用化学等各个领域. 因此, 开发高效、便捷地制备硫代磷酸酯的方法在磷化学研究中具有重要意义. 近年来, 随着可持续化学发展的要求, 可见光和电催化有机合成作为绿色友好的策略引起了化学家们的广泛关注. 本综述介绍了光/电合成硫代磷酸酯类化合物的研究进展, 包括无金属光催化、金属光催化、染料光催化、光氧化还原和金属协同催化的新型光催化反应以及无外部金属和催化剂的电氧化反应.

关键词: 光催化, 电催化, 硫代磷酸酯, 合成方法

Phosphorothioates are a class of organophosphates containing S—P(O) bonds, which have important chemical and biological properties and are widely used in various fields such as organic synthesis, medicinal chemistry and agricultural chemistry. Therefore, the development of efficient and convenient methods for the preparation of phosphorothioates and their derivatives is of great significance in the research of phosphorus chemistry. In recent years, with the requirements of sustainable chemical development, photocatalysis and electrocatalysis as green and friendly strategies have attracted wide attention from chemists. This review introduces the research progress of photosynthesis of phosphorothioates, including metal-free photocatalysis, metal photocatalysis, dye photocatalysis, photoredox and metal co-catalysis, and electrooxidation reactions without external metals and catalysts.

Key words: photocatalysis, electrocatalysis, phosphorothioates, synthesis method

引用此文

郭国菊, 吴启龙, 董宇振, 张洁, 石永佳, 柳清, 杨道山. 光/电化学驱动硫代磷酸酯类化合物的合成研究进展[J]. 有机化学, 2025, 45(10): 3719-3740.

Guoju Guo, Qilong Wu, Yuzhen Dong, Jie Zhang, Yongjia Shi, Qing Liu, Daoshan Yang. Research Progress in the Synthesis of Phosphorothioates Driven by Photo/Electrochemistry[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3719-3740.

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图/表 26

图1. 硫代磷酸酯类化合物在医药和农药中的应用

Figure 1. Application of thiophosphate in medicine and pesticides

图式1. 可见光/RB催化硫酚与二苯基氧磷的交叉脱氢反应

Scheme 1. Visible light/RB-catalyzed cross dehydrogenation of thiophenol with diphenyl-phosphorus oxide

图式2. 可见光/MB催化的硫酚与二苯基氧磷的交叉脱氢反应

Scheme 2. Visible light/MB-catalyzed cross dehydrogenation of thiophenol with diphenyl-phosphorus oxide

图式3. 可见光介导的硫酚类Arbuzov反应

Scheme 3. Visible-light mediated Arbuzov-like reaction with thiophenols

图式4. 可见光/吖啶盐催化位点选择性芳烃C(sp2)—H硫代磷酸化反应

Scheme 4. Visible light/acridine salts catalyzed site-selective C(sp2)—H thiophosphorylation of aromatic hydrocarbons

图式5. 可见光光氧化还原催化炔烃与喹喔啉酮, P4S10和醇的双官能化反应

Scheme 5. Visible-light photoredox-catalyzed difunctionalization of alkynes with quinoxalin-2(1H)-ones, P4S10, and alcohols

图式6. 可见光/铱催化通过三组分反应合成硫代磷酸酯

Scheme 6. Thiophosphate synthesized by three-component reaction under visible light/iridium catalysis

图式7. 可见光/铱催化NHPI酯与硫代磷酸酯的交叉偶联

Scheme 7. Visible light/Ir catalyzed cross-coupling of NHPI esters and thiophosphates

图式8. 可见光/铜催化下硫代磷酸酯的芳基化和烯基化反应

Scheme 8. Visible light/copper catalysis-enabled arylation and alkenylation of phosphorothioates via site-selective C—H thianthrenation

图式9. 含氟S-烷基硫代酸磷酯和二硫代酸磷酯的模块化合成

Scheme 9. Modular synthesis of fluorine-containing S-alkyl phosphorothioates and phosphorodithioates

图式10. 通过光氧化还原/铜催化远程C(sp3)—H磷硫基化N-烷氧基吡啶盐合成δ-磷硫基醇和硫代磷系四氢呋喃

Scheme 10. Synthesis of δ-phosphorothiolated alcohols and phosphorothio-tethered tetrahydrofurans by photoredox/copper catalyzed remote C(sp3)—H phosphorothiolation of N-alkoxypyridinium salts

图式11. 使用末端炔烃和(iPrO)2P(O)SH通过可见光诱导的交叉脱氢偶联反应

Scheme 11. Visible light-induced cross-dehydrogenative coupling reactions using terminal alkynes and (iPrO)2P(O)SH

图式12. 光氧化还原和铁(II)协同催化乙烯基芳烃的碳磷硫代化

Scheme 12. Synergistic photoredox and iron(II) catalyzed carbophosphorothiolation of vinyl arenes

图式13. 可见光促进的光氧化和镍催化三甲基甲硅烷基硫醚和P(O)H化合物的交叉偶联

Scheme 13. Visible-light-promoted photooxidation and nickel-catalyzed cross-coupling of trimethylsilyl sulfide and P(O)H compounds

图式14. 铜催化炔烃氟烷基硫代磷酸化合成(E)-β-氟烷基乙烯基硫代磷酸酯

Scheme 14. Copper-catalyzed fluoroalkylphosphorothiolation of alkynes for the synthesis of (E)‑β-fluoroalkyl vinyl phosphorothioates

图式15. 光氧化还原和铜催化烯烃磺酰基磷硫基化生成β-磺酰基磷硫酸酯

Scheme 15. Photoredox and copper-catalyzed sulfonylphosphorothiolation of alkenes toward β-sulfonyl phosphorothioates

图式16. 通过光氧化还原/铜催化串联反应构建磷硫代2-吡咯烷酮

Scheme 16. Construction of phosphorothiolated 2-pyrrolidinones via photoredox/copper-catalyzed cascade reaction

图式17. 光氧化还原/铜双催化炔丙基衍生物的硫代磷酸酯化反应

Scheme 17. Photoredox/copper dual-catalyzed phosphorothiolation of propargylic derivatives

图式18. 蓝光led促进硫代磷酸酯类化合物的合成

Scheme 18. Blue LED-promoted syntheses of phosphorothioates

图式19. 使用元素硫作为硫源获得S-烷基磷酸酯的可见光驱动的多组分反应

Scheme 19. Visible-light-driven multicomponent reactions to access S-alkyl phosphorothioates using elemental sulfur as the sulfur source

图式20. 烯基和1,3-二烯基溴的光化学卤键辅助碳硫代磷酰化反应

Scheme 20. Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides

图式21. 硫醇的电化学脱氢磷酸化

Scheme 21. Electrochemical dehydrogenative phosphorylation of thiols

图式22. 吲嗪与硫氰酸盐和(RO)2P(O)H的电化学C—H硫代磷酸酯化反应

Scheme 22. Electrochemical C—H phosphorothiolation of indolizines with thiocyanate and (RO)2P(O)H

图式23. 通过电氧化和超声波辐射的协同作用实现(杂)芳烃的区域选择性C—H硫代磷酸酯化

Scheme 23. Regioselective C—H phosphorothiolation of (hetero)arenes enabled by the synergy of electrooxidation and ultrasonic irradiation

图式24. 无电解质条件下电化学活化的2H-吲唑脱氢硫代磷酸酯

Scheme 24. Electrochemically enabled dehydrogenative phosphorothiolation of 2H-indazoles under electrolyte-free condition

图式25. 电化学硫代磷酸酯化: 合成硫代磷酸酯取代吲嗪的方法

Scheme 25. Electrochemical phosphorothiolation: access to phosphorothiolated substituted indolizines

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光/电化学驱动硫代磷酸酯类化合物的合成研究进展

Research Progress in the Synthesis of Phosphorothioates Driven by Photo/Electrochemistry

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