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Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate.
Lu, Ling-Hui; Ou, Guangchuan; Zhao, Xiongjie; Wang, Yufei; Chen, Xuelian; Liao, Wenjun; Li, Shundan; Wu, Chao.
Afiliación
  • Lu LH; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
  • Ou G; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
  • Zhao X; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
  • Wang Y; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
  • Chen X; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
  • Liao W; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
  • Li S; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
  • Wu C; College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China. chwu_chem@yeah.net.
Org Biomol Chem ; 19(37): 8128-8132, 2021 09 29.
Article en En | MEDLINE | ID: mdl-34473178
ABSTRACT
A convenient and efficient approach to (E)-2-iodo-3-(methylthio)acrylate has been developed through direct iodothiomethylation of alkynes with aqueous HI and DMSO under mild conditions. This novel protocol has demonstrated a unique difunctionalization of electron-deficient alkynes with a broad substrate scope and excellent functional-group tolerance. Preliminary mechanistic studies indicated that prior diiodination of alkynes, followed by nucleophilic substitution with in situ generated DMS led to the formation of (E)-2-iodo-3-(methylthio)acrylate.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Alquinos / Yodo Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: China
Texto completo
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XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Alquinos / Yodo Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: China