Rahul Kumar Saini, Paran J. Borpatra, Satyendra Kumar Pandey
{"title":"Annulative Coupling of Sulfoxonium Ylides with Aldehydes and Naphthols or Coumarins: Easy Access to Fused Dihydrofurans","authors":"Rahul Kumar Saini, Paran J. Borpatra, Satyendra Kumar Pandey","doi":"10.1021/acs.joc.4c02787","DOIUrl":null,"url":null,"abstract":"We present a novel, metal- and additive-free method for the robust synthesis of dihydrofuran-fused naphthalenes and coumarins. This approach utilizes the annulative coupling of sulfoxonium ylides with aldehydes, naphthols, or coumarins at ambient temperature. The method exhibits broad substrate compatibility, accommodating various functional groups on sulfoxonium ylides and naphthol or coumarin derivatives and resulting in good to high yields of the desired products. Additionally, we successfully scaled up the reactions, and the synthesized derivatives were further converted to other valuable bioactive molecules, validating the viability of our approach.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02787","RegionNum":2,"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
We present a novel, metal- and additive-free method for the robust synthesis of dihydrofuran-fused naphthalenes and coumarins. This approach utilizes the annulative coupling of sulfoxonium ylides with aldehydes, naphthols, or coumarins at ambient temperature. The method exhibits broad substrate compatibility, accommodating various functional groups on sulfoxonium ylides and naphthol or coumarin derivatives and resulting in good to high yields of the desired products. Additionally, we successfully scaled up the reactions, and the synthesized derivatives were further converted to other valuable bioactive molecules, validating the viability of our approach.
期刊介绍:
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.