Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel·lí Domingo 1, 43007 Tarragona, Spain.
J Org Chem. 2022 Aug 19;87(16):10791-10806. doi: 10.1021/acs.joc.2c01038. Epub 2022 Aug 9.
The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF and SCFH moieties. Herein, two saccharin-based electrophilic reagents have been disclosed for the incorporation of uncommon SCFCFH and SCFCF motifs. Their reactivity performance, multigram-scale preparation, and divergent derivatization have been thoroughly investigated with a variety of nucleophiles, including natural products and pharmaceuticals.
氟烷基硫醚基团的引入引起了药物发现界的关注，因为它们赋予了生物活性化合物特殊的物理化学和药代动力学特性，但这些通常仅限于标准的 SCF 和 SCFH 部分。本文中，作者公开了两种基于磺酰亚胺的亲电试剂，用于引入不常见的 SCFCFH 和 SCFCF 基序。它们的反应性能、多克级制备以及与各种亲核试剂（包括天然产物和药物）的衍生化已经得到了彻底的研究。
