{"title":"PIFA-Mediated C─H Thiolation and Selenylation of Pseudo-Anomeric Position of Glycals with Disulfides or Diselenides at Room Temperature","authors":"Neha Singh Chauhan, Dr. Pintu Kumar Mandal","doi":"10.1002/ajoc.202500291","DOIUrl":null,"url":null,"abstract":"<p>Herein, we report the [Bis(trifluoroacetoxy)iodo]benzene mediated C(sp<sup>2</sup>)−H bond thiolation and selenylation of <i>pseudo</i>-anomeric position of C2-branched glycals using sugar, aliphatic, and aromatic disulfides or diselenides partner at room temperature. This developed protocol offers a metal-free synthetic route that potentiates the generation of a library of 1-thiotrehaloses and thio/selenoglycosides bearing a variety of functional groups in moderate to good yields. Concerning the glycal partners, the peracetylated protected analogue showed a similar reactivity like the benzylated model substrates under this conditions. Based on control experiments, a plausible radical pathway mechanism is proposed.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7000,"publicationDate":"2025-07-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://aces.onlinelibrary.wiley.com/doi/10.1002/ajoc.202500291","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report the [Bis(trifluoroacetoxy)iodo]benzene mediated C(sp2)−H bond thiolation and selenylation of pseudo-anomeric position of C2-branched glycals using sugar, aliphatic, and aromatic disulfides or diselenides partner at room temperature. This developed protocol offers a metal-free synthetic route that potentiates the generation of a library of 1-thiotrehaloses and thio/selenoglycosides bearing a variety of functional groups in moderate to good yields. Concerning the glycal partners, the peracetylated protected analogue showed a similar reactivity like the benzylated model substrates under this conditions. Based on control experiments, a plausible radical pathway mechanism is proposed.
期刊介绍：
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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