Citation: Ze-Yuan Ma, Mei Xiao, Cheng-Kun Li, Adedamola Shoberu, Jian-Ping Zou. S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds[J]. Chinese Chemical Letters, ;2024, 35(5): 109076. doi: 10.1016/j.cclet.2023.109076 shu

S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Suzhou 215123, China

jpzou@suda.edu.cn

Received Date: 17 June 2023
Revised Date: 2 September 2023
Accepted Date: 7 September 2023
Available Online: 9 September 2023

Figures(8)

An efficient synthesis of the electrophilic reagent, S-(1,3-dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP) is described. Moreover, the synthetic applications of SDDP wherein the transfer of the SP(O)(OEt)₂ moiety occurs were investigated. In this manner, SDDP underwent facile SP(O)(OEt)₂ transfer with electron-rich substrates such as ketones, indoles, and thiols to form α-phosphorothiolated ketones, 3-phosphorothiolated indoles and S-phosphorothiolated thioethers, respectively.
- Electrophilic reagent,
- Phosphorothiolation,
- Electrophilic substitution
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