A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide.

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2024-10-30 DOI:10.1021/acs.joc.4c01644
Padma Priya V R, Antony Haritha Mercy A, Natarajan K, Sugapriya S, Ganesh Chandra Nandi
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引用次数: 0

Abstract

We develop a rapid and mild protocol to access sulfonimidoyl fluoride-[S(VI)] from sulfenamide-[S(II)] directly. The transformation occurs via the reaction of sulfenamide with NCS (N-chlorosuccinimide), water, and TBAF in acetonitrile. Water and TBAF act as the source for S═O bond formation and fluoride, respectively. The reaction takes a very short time (within 5 min). The drug molecules, such as Carbamazepine and Levetiracetam attached sulfonimidoyl fluorides are also achieved following this protocol. Furthermore, sulfonimidoyl fluoride is transformed into sulfonimidamide in the presence of AlCl3. To the best of our knowledge, it is the first report detailing the synthesis of sulfonimidoyl fluoride-[S(VI)] directly from S(II)-sulfenamide.

Abstract Image

从磺酰胺制备磺酰亚胺基氟化物的快速、温和且直接的途径。
我们开发了一种快速、温和的方法,可直接从磺酰胺-[S(II)]中获得磺酰亚胺酰氟-[S(VI)]。磺酰胺与 NCS(N-氯代丁二酰亚胺)、水和 TBAF 在乙腈中发生反应,从而实现转化。水和 TBAF 分别是 S═O 键形成和氟化物的来源。反应时间很短(5 分钟内)。药物分子(如卡马西平和左乙拉西坦)附着的磺酰亚胺酰氟化物也是通过该方案实现的。此外,磺酰亚胺酰氟还能在 AlCl3 的存在下转化为磺酰亚胺。据我们所知,这是首次详细报道直接从 S(II)-亚磺酰胺合成磺酰亚胺酰氟-[S(VI)]。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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