通过芳基炔诱导的[2,3]史蒂文斯重排反应合成功能化的β-酮芳硫醚。
Synthesis of Functionalized β-Keto Arylthioethers by the Aryne Induced [2,3] Stevens Rearrangement of Allylthioethers.
机构信息
Organic Chemistry Division, CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road, Pune 411008, India.
Academy of Scientific and Innovative Research (AcSIR) , New Delhi 110020, India.
出版信息
J Org Chem. 2017 Apr 21;82(8):4470-4476. doi: 10.1021/acs.joc.7b00479. Epub 2017 Apr 3.
A mild and transition-metal-free synthesis of β-keto arylthioethers has been developed by the aryne triggered [2,3] Stevens rearrangement of allylthioethers. The key sulfur ylide intermediate for the rearrangement was formed by the S-arylation of allylthioethers with arynes generated from 2-(trimethylsilyl)aryl triflates using CsF. Later, the reaction products are converted into valuable heterocycles in two steps.
一种温和的、无需过渡金属的β-酮芳硫醚的合成方法，通过芳炔引发的烯丙基硫醚[2,3]史蒂文斯重排反应实现。重排过程中的关键硫叶立德中间体是通过用氟化铯（CsF）处理 2-（三甲基甲硅烷基）芳基三氟甲磺酸酯生成的芳炔与烯丙基硫醚的 S-芳基化反应形成的。随后，两步反应可将产物转化为有价值的杂环化合物。
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