Chemoselective Thioacylation of Amines Enabled by Synergistic Defluorinative Coupling,Organic Letters

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Chemoselective Thioacylation of Amines Enabled by Synergistic Defluorinative Coupling
Organic Letters ( IF 4.9 ) Pub Date : 2024-07-24 , DOI: 10.1021/acs.orglett.4c02237
Yuqi Li ₁ , Tongxiang Cao ₁ , Rongbin Peng ₁ , Shang Zhou ₁ , Xujing Long ₁ , Huanfeng Jiang ₁ , Chuanle Zhu _{1,

2}

Affiliation

A mild and chemoselective method for the thioacylation of amines, including amino acids and peptides, using gem-difluoroalkenes and sulfide, is reported. The distinguishing of the different nucleophilic sites (S-site and diverse N-sites) by the chemoselective C–F bond functionalization of gem-difluoroalkenes enables the unique synergistic defluorinative coupling reaction. This reaction features mild conditions, is operationally simple, efficient, and gram-scalable, tolerates various functional groups, and is activator-free and without racemization. Thioamide moieties were incorporated site-specifically into bioactive compounds. The proposed mechanism is illustrated by a DFT calculation.

中文翻译：

协同脱氟偶联实现胺的化学选择性硫酰化

报道了一种使用偕二氟烯烃和硫化物对胺（包括氨基酸和肽）进行硫代酰化的温和且化学选择性的方法。通过宝石二氟烯烃的化学选择性 C-F 键功能化来区分不同的亲核位点（ S位点和不同的N位点），从而实现独特的协同脱氟偶联反应。该反应条件温和、操作简单、高效、克级放大、耐受多种官能团、不含活化剂、无外消旋化。硫代酰胺部分被定点地掺入生物活性化合物中。所提出的机制通过 DFT 计算来说明。

更新日期：2024-07-24

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