{"title":"Microwave-assisted safe and efficient synthesis of α-ketothioesters from acetylenic sulfones and DMSO","authors":"Jiayi Wang , Duo Fu , Jiaxi Xu","doi":"10.1080/17415993.2022.2137414","DOIUrl":null,"url":null,"abstract":"<div><p>α-Ketothioesters are safely and efficiently synthesized from arylacetylenic sulfones and dimethyl sulfoxide (DMSO) in the presence of equivalent of water and catalytic amount of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) under microwave irradiation. Arylacetylenic sulfones and dimethyl sulfoxide first form arenecarbonyl sulfonyl dimethylsulfonium methylides via nucleophilic addition, ring closure, and 4e ring opening. The methylides undergo a radical process to generate α-methylthio-α-sulfonylacetophenones, which further convert to α-ketothioesters through the Pummerer oxidation. Compared to the previous methods, the current method is safer and more efficient.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 2","pages":"Pages 232-247"},"PeriodicalIF":2.1000,"publicationDate":"2023-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Sulfur Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1741599323000582","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 2
Abstract
α-Ketothioesters are safely and efficiently synthesized from arylacetylenic sulfones and dimethyl sulfoxide (DMSO) in the presence of equivalent of water and catalytic amount of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) under microwave irradiation. Arylacetylenic sulfones and dimethyl sulfoxide first form arenecarbonyl sulfonyl dimethylsulfonium methylides via nucleophilic addition, ring closure, and 4e ring opening. The methylides undergo a radical process to generate α-methylthio-α-sulfonylacetophenones, which further convert to α-ketothioesters through the Pummerer oxidation. Compared to the previous methods, the current method is safer and more efficient.
期刊介绍：
The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science.
Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.
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