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通过1,3 - 二硫戊环的碱介导碎片化反应合成二硫酯衍生物

Synthesis of Dithioester Derivatives by Base-Mediated Fragmentation of 1,3-Dithiolanes.

作者信息

Pelit Hasan, Sinmaz Mehmet Aytug, Ildem Oyku Acelya, Mert Zeynep, Turhan Yigit Efe, Aydin Elif, Yilmaz Senem Dila, Mentese Andrea, Yucel Baris

机构信息

Istanbul Technical University, Science Faculty, Department of Chemistry, Istanbul 34469, Türkiye.

出版信息

Org Lett. 2025 Apr 25;27(16):4135-4139. doi: 10.1021/acs.orglett.5c00666. Epub 2025 Apr 14.

DOI:10.1021/acs.orglett.5c00666
PMID:40226849
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12038844/
Abstract

Dithioesters are important agents for chain transfer in polymer chemistry and precursors in the synthesis of heterocycles. Straightforward approaches to their synthesis are therefore in demand. Outlined herein is a method to access such compounds in one-pot. 2-Aryl-1,3-dithiolanes undergo ring fragmentation with LiHMDS in CPME to generate aryl-dithiocarboxylates in 5 min at 100 °C. These anions are subsequently captured in the second step by addition of various alkyl halides and diaryliodonium salts to furnish a large library of dithioesters in good yields. The method can be also employed in a one-pot, one-step manner for alkyl bromides and allows the synthesis of dithioesters in gram scale.

摘要

二硫酯是聚合物化学中重要的链转移剂和杂环合成的前体。因此，需要直接的合成方法。本文概述了一种一锅法制备此类化合物的方法。2-芳基-1,3-二硫戊环在CPME中与LiHMDS发生环断裂，在100℃下5分钟内生成芳基二硫代羧酸盐。这些阴离子随后在第二步中通过加入各种卤代烃和二芳基碘鎓盐被捕获，以高收率提供大量的二硫酯库。该方法也可用于溴代烃的一锅一步法，并可克级规模合成二硫酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/4eef74559194/ol5c00666_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/cc50a6d5910f/ol5c00666_0001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/4eef74559194/ol5c00666_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/cc50a6d5910f/ol5c00666_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/7b8acdb28972/ol5c00666_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/26e0afa91b32/ol5c00666_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/fbb3d6cc4580/ol5c00666_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/4e0d82582a37/ol5c00666_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f268/12038844/4eef74559194/ol5c00666_0006.jpg

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J Org Chem. 2024 Sep 6;89(17):12785-12789. doi: 10.1021/acs.joc.4c01222. Epub 2024 Aug 20.
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Synthesis of 3,5-Disubstituted-1,2,4-thiadiazoles via NaH-DMF-Promoted Dehydrogenative Intramolecular N-S Bond Formation.通过NaH-DMF促进的分子内脱氢N-S键形成合成3,5-二取代-1,2,4-噻二唑
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Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives.
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Metal-Free -Arylation of Phosphorothioate Diesters and Related Compounds with Diaryliodonium Salts.无金属 - 用二芳基碘鎓盐对硫代磷酸酯二酯和相关化合物进行芳基化反应。
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