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

• Published in: Chinese chemical letters Vol. 35; no. 5; pp. 109076 - 154
• Main Authors: Ma, Ze-Yuan, Xiao, Mei, Li, Cheng-Kun, Shoberu, Adedamola, Zou, Jian-Ping
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.05.2024; Key Laboratory of Organic Synthesis of Jiangsu Province,College of Chemistry and Chemical Engineering,Soochow University,Suzhou 215123,China
• Subjects: Electrophilic reagent; Electrophilic substitution; Phosphorothiolation; Electrophilic substitution; Electrophilic reagent; Phosphorothiolation
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2023.109076

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. 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 ɑ-phosphorothiolated ketones, 3-phosph. [Display omitted]