Citation: LIANG Hongwen, ZHANG Liangliang, TANG Guo. Synthesis of S-Alkyl Phosphorothioates from Alkyl Cholorides, Phosphites and Sulfur Powder[J]. Chinese Journal of Applied Chemistry, ;2019, 36(7): 764-772. doi: 10.11944/j.issn.1000-0518.2019.07.180365 shu

Synthesis of S-Alkyl Phosphorothioates from Alkyl Cholorides, Phosphites and Sulfur Powder

a.
Xiamen No.1 High School of Fujian, Fujian, Xiamen 361003, China
b.
College of Chemistry and Chemical Engineering, Xiamen University, Fujian, Xiamen 361005, China

Corresponding author: TANG Guo, t12g21@xmu.edu.cn
Received Date: 14 November 2018
Revised Date: 10 December 2018
Accepted Date: 28 January 2019

Fund Project: Supported by the National Natural Science Foundation of Chian(No.21772163)the National Natural Science Foundation of Chian 21772163

Figures(2)

Organophosphorus compounds bearing C-S-P(O) bonds have received increasing attention due to their well-documented biological properties in the fields of pharmaceuticals and agrochemicals. We have developed a novel, simple and efficient carbon (alkyl)-sulfur-phosphorus bond-forming reaction to access S-alkyl phosphorothioates. This transformation would provide a new pathway for the formation of P-S and C-S bonds in one reaction. Altogether, seventeen S-benzyl phosphothioates were prepared in 70%~99% yields by a one-pot CsCO₃-promoted coupling reaction of benzyl chloride, elemental sulfur, and H-phosphonates. Among them, thirteen pharmacologically and synthetically important S-alkyl phosphorothioates were synthesized in 45%~93% yields under air in the presence of triethylamine without any transition metal catalysts. In addition, utilization of common and readily available sulfur powder (S₈) and R₂P(O)H compounds as the components should make this multicomponent reaction much more attractive both fundamentally and synthetically.
- agrochemicals,
- phosphorothioates,
- sulfur powder,
- phosphites,
- alkyl chlorides
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沈阳化工大学材料科学与工程学院沈阳 110142