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

doi:10.6023/cjoc202410018

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3719-3740.DOI: 10.6023/cjoc202410018 Previous Articles Next Articles

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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

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)

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

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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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Fig. & Tab. 26

Figure 1. Application of thiophosphate in medicine and pesticides

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 18. Blue LED-promoted syntheses of phosphorothioates

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

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

Scheme 21. Electrochemical dehydrogenative phosphorylation of thiols

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

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

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

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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[15]	Yongmei Li, Liangbo Sun, Kun Xu, Chengchu Zeng. Recent Advances toward Electro- and Electrophotochemical 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Catalyzed C—H/C—F Bonds Functionalization [J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 668-676.