Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate,Organic & Biomolecular Chemistry

当前位置： X-MOL 学术 › Org. Biomol. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-08-26 , DOI: 10.1039/d1ob01287h
Ling-Hui Lu ₁ , Guangchuan Ou ₁ , Xiongjie Zhao ₁ , Yufei Wang ₁ , Xuelian Chen ₁ , Wenjun Liao ₁ , Shundan Li ₁ , Chao Wu ₁

Affiliation

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.

中文翻译：

缺电子炔烃的选择性双官能化：获得（E）-2-碘-3-（甲硫基）丙烯酸酯

通过在温和条件下用 HI 和 DMSO 水溶液直接碘硫甲基化炔烃，开发了一种方便有效的 ( E )-2-iodo-3-(甲硫基)丙烯酸酯方法。这种新颖的协议证明了缺电子炔烃的独特双功能化，具有广泛的底物范围和出色的官能团耐受性。初步机理研究表明，先对炔烃进行二碘化，然后用原位产生的 DMS 进行亲核取代，导致形成 ( E )-2-iodo-3-(methylthio) 丙烯酸酯。

更新日期：2021-09-02

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11