β-硫代酰胺的无金属α-磺酰化：获得α-磺酰基-β-酮酰胺及其光物理研究

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-10-14 DOI:10.1002/ejoc.202401098

Vipin Kumar, Monish Ansari, Anup Yadav, Saurabh Singh, Krishanu Bandyopadhyay, Satyen Saha, Maya Shankar Singh

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引用次数: 0

摘要

在此，我们首次报道了一种不含金属和添加剂的β-硫代酮酰胺与磺酰氯的空前反应性，该反应通过硫代酰胺到酰胺的原位转化，然后在室温露天下进行脱氢卤化C-S交叉偶联，合成了之前未报道过的2-磺酰基-3-氧代-N,3-二丙基酰胺。该方法不仅操作简单、效率高、条件温和、可扩展性强，而且易于以良好至高产率获得多种α-磺酰基-β-酮酰胺。此外，DFT 和光物理研究支持了所提出的机理，并揭示了合成的砜类化合物与 ESPT 相耦合的独特的激发依赖性发射。

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Metal-Free α-Sulfonylation of β-Ketothioamides: Access to α-Sulfonyl-β-Ketoamides and their Photophysical Studies

Herein, we report a metal and additive-free unprecedented reactivity of β-ketothioamides with sulfonyl chlorides for the synthesis of previously unreported 2-sulfonyl-3-oxo-N,3-diarylpropanamides via in situ thioamide to amide conversion followed by dehydrohalogenative C-S cross-coupling at room temperature under an open air for the first time. The protocol demonstrates not only its operational simplicity, efficiency, mild condition, and scalability, but also easy to get the diverse α-sulfonyl-β-ketoamides in good to high yields. Additionally, the DFT and photophysical studies supported the proposed mechanism, and revealed unique excitation-dependent emission coupled with ESPT for the synthesized sulfones.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.