{"title":"One-pot chemoselective aerobic synthesis of allyl-aryl sulfinyls by photoinduced Na<sub>2</sub> - eosin Y.","authors":"Trinadh Ballanki, Aishwarya Subramanian, Baby Viswambharan","doi":"10.1039/d5ob00181a","DOIUrl":null,"url":null,"abstract":"<p><p>Allyl-aryl sulfinyls are ubiquitous in medicine as well as in catalysis. Chemoselective synthesis of allyl-aryl sulfinyls is challenging due to competitive isomerization and overoxidation of allylic C-H bonds as well as sulfur. Herein, we have accomplished an unprecedented, metal-free, one-pot protocol for the aerobic synthesis of allyl-aryl sulfinyls from Morita-Baylis-Hillman allyl bromides and thiols under visible light photocatalysis through a radical pathway. Interestingly, this selective and controlled oxidation of <i>in situ</i>-formed allyl-aryl sulfides by the sub-stoichiometric oxidizing agent TEMPO <i>via</i> visible-light photocatalysis is well tolerated by an array of allyl bromides and thiols. This approach provides an efficient one-step route to the anti-cancer molecule INF<sub>50</sub>, and its synthetic application is demonstrated by an interrupted Pummerer reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5ob00181a","RegionNum":3,"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
Allyl-aryl sulfinyls are ubiquitous in medicine as well as in catalysis. Chemoselective synthesis of allyl-aryl sulfinyls is challenging due to competitive isomerization and overoxidation of allylic C-H bonds as well as sulfur. Herein, we have accomplished an unprecedented, metal-free, one-pot protocol for the aerobic synthesis of allyl-aryl sulfinyls from Morita-Baylis-Hillman allyl bromides and thiols under visible light photocatalysis through a radical pathway. Interestingly, this selective and controlled oxidation of in situ-formed allyl-aryl sulfides by the sub-stoichiometric oxidizing agent TEMPO via visible-light photocatalysis is well tolerated by an array of allyl bromides and thiols. This approach provides an efficient one-step route to the anti-cancer molecule INF50, and its synthetic application is demonstrated by an interrupted Pummerer reaction.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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