Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate. Issue 37 (2nd September 2021)

• Record Type: Journal Article
• Authors: Lu, Ling-Hui; Ou, Guangchuan; Zhao, Xiongjie; Wang, Yufei; Chen, Xuelian; Liao, Wenjun; Li, Shundan; Wu, Chao
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 37(2021)
• Page Start: 8128
• Page End: 8132
• Publication Date: 2021-09-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01287h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A convenient and efficient approach to ( E )-2-iodo-3-(methylthio)acrylate has been developed through direct iodothiomethylation of electron-deficient alkynes with aqueous HI and DMSO under mild conditions. 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.