{"title":"First synthesis of (difluoroiodomethyl)thiophenes through double iodation of 2-(difluoromethylene)but-3-yn-1-yl benzyl sulfides†","authors":"Daiki Komatsu , Takeshi Hanamoto","doi":"10.1039/d5ob00152h","DOIUrl":null,"url":null,"abstract":"<div><div>The Sonogashira cross-coupling of 2-bromo-3,3-difluoroallyl benzyl sulfide with various terminal acetylenes afforded the corresponding 2-(difluoromethylene)but-3-yn-1-yl benzyl sulfides in acceptable to good yields. Subsequent double iodation of the enyne sulfides in a mixed solvent (CHCl<sub>3</sub>/EtOH = 50/1) provided promising 4-(difluoroiodomethyl)-3-iodo-2-substituted thiophenes in good to excellent yields.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 12","pages":"Pages 2883-2890"},"PeriodicalIF":2.7000,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025001314","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/21 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The Sonogashira cross-coupling of 2-bromo-3,3-difluoroallyl benzyl sulfide with various terminal acetylenes afforded the corresponding 2-(difluoromethylene)but-3-yn-1-yl benzyl sulfides in acceptable to good yields. Subsequent double iodation of the enyne sulfides in a mixed solvent (CHCl3/EtOH = 50/1) provided promising 4-(difluoroiodomethyl)-3-iodo-2-substituted thiophenes in good to excellent yields.
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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