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磺酸电化学脱水制备其酸酐

Electrochemical Dehydration of Sulfonic Acids to Their Anhydrides.

作者信息

Lunghi Enrico, van Koten Annemijn M, Schneider Johannes, Waldvogel Siegfried R

机构信息

Max-Planck-Institute for Chemical Energy Conversion (MPI CEC), Stiftstraße 34-36, Mülheim an der Ruhr 45470, Germany.

Department of Chemistry, Johannes Gutenberg University (JGU), Duesbergweg 10-14, Mainz 55128, Germany.

出版信息

J Org Chem. 2025 Sep 5;90(35):12259-12264. doi: 10.1021/acs.joc.5c01155. Epub 2025 Aug 22.

Abstract

We developed an electrochemical method for sulfonic anhydride synthesis and one-pot derivatization into sulfonamides and mesylates under mild conditions. Aliphatic sulfonic anhydrides were electrogenerated in up to a 74% yield. Since isolating these moisture-sensitive intermediates is challenging, the in situ-generated sulfonic anhydrides were directly converted into sulfonamides or alkyl sulfonates using amines or alcohols, respectively. This scalable process enables the synthesis of various nitrogen- and oxygen-based products in the multigram range.

摘要

我们开发了一种电化学方法用于磺酸酐的合成,并在温和条件下将其一锅法衍生化为磺酰胺和甲磺酸盐。脂肪族磺酸酐的电合成产率高达74%。由于分离这些对水分敏感的中间体具有挑战性,原位生成的磺酸酐分别使用胺或醇直接转化为磺酰胺或烷基磺酸盐。这种可扩展的方法能够合成多克规模的各种含氮和含氧产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/646b/12418306/809bd79ed6bf/jo5c01155_0001.jpg

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