{"title":"Room-Temperature Ligation of Iminophosphoranes with gem-Difluoroalkenes","authors":"Masaru Tanioka, Fuudai Enomoto, Fumino Kitamura, Ryunosuke Nakamura, Akinari Takano, Shohei Kanayama, Aki Kohyama, Tsuyoshi Yamada, Yuji Matsuya","doi":"10.1021/acs.joc.4c02874","DOIUrl":null,"url":null,"abstract":"Ligation reactions that proceed at room temperature under aqueous conditions and without catalysts are in high demand, including bioorthogonal reactions. We report a mild amide-ligation reaction of iminophosphoranes with <i>gem</i>-difluoroalkenes. Through experimental and theoretical analyses of intermolecular and intramolecular amidation reactions, we found that the Staudinger–Bertozzi ligation-type reaction of iminophosphoranes with <i>gem</i>-difluoroalkenes is an excellent reaction that proceeds rapidly at room temperature in an aqueous solvent.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-03-02","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.4c02874","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
Ligation reactions that proceed at room temperature under aqueous conditions and without catalysts are in high demand, including bioorthogonal reactions. We report a mild amide-ligation reaction of iminophosphoranes with gem-difluoroalkenes. Through experimental and theoretical analyses of intermolecular and intramolecular amidation reactions, we found that the Staudinger–Bertozzi ligation-type reaction of iminophosphoranes with gem-difluoroalkenes is an excellent reaction that proceeds rapidly at room temperature in an aqueous solvent.
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.
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