S-(1,3-Dioxoisoindolin-2-yl)O,O‑diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds
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 t...
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| Published in | Chinese chemical letters Vol. 35; no. 5; pp. 109076 - 154 |
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| Main Authors | , , , , |
| 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 |
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| Abstract | 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] |
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| AbstractList | An efficient synthesis of the electrophilic reagent,S-(1,3-dioxoisoindolin-2-yl)O,O-diethyl phosphoroth-ioate(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 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] |
| ArticleNumber | 109076 |
| Author | Li, Cheng-Kun Zou, Jian-Ping Xiao, Mei Ma, Ze-Yuan Shoberu, Adedamola |
| AuthorAffiliation | Key Laboratory of Organic Synthesis of Jiangsu Province,College of Chemistry and Chemical Engineering,Soochow University,Suzhou 215123,China |
| AuthorAffiliation_xml | – name: Key Laboratory of Organic Synthesis of Jiangsu Province,College of Chemistry and Chemical Engineering,Soochow University,Suzhou 215123,China |
| Author_xml | – sequence: 1 givenname: Ze-Yuan surname: Ma fullname: Ma, Ze-Yuan – sequence: 2 givenname: Mei surname: Xiao fullname: Xiao, Mei – sequence: 3 givenname: Cheng-Kun surname: Li fullname: Li, Cheng-Kun – sequence: 4 givenname: Adedamola surname: Shoberu fullname: Shoberu, Adedamola – sequence: 5 givenname: Jian-Ping orcidid: 0000-0002-8092-9527 surname: Zou fullname: Zou, Jian-Ping email: jpzou@suda.edu.cn |
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| Keywords | Electrophilic substitution Electrophilic reagent Phosphorothiolation |
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| Snippet | An efficient synthesis of the electrophilic reagent, S-(1,3-dioxoisoindolin-2-yl)O,O‑diethyl phosphorothioate (SDDP) is described. Moreover, the synthetic... An efficient synthesis of the electrophilic reagent,S-(1,3-dioxoisoindolin-2-yl)O,O-diethyl phosphoroth-ioate(SDDP)is described.Moreover,the synthetic... |
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| SubjectTerms | Electrophilic reagent Electrophilic substitution Phosphorothiolation |
| Title | S-(1,3-Dioxoisoindolin-2-yl)O,O‑diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds |
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