{"title":"Base-Dependent Divergent Carbodifluoroalkylation and Halodifluoroalkylation of Alkenes under Visible-Light Irradiation.","authors":"Lin Tang, Fengjuan Jia, Lufang Zhang, Taijun Wu, Xinmeng Wei, Lingyun Zheng, Qiuju Zhou","doi":"10.1021/acs.joc.4c01591","DOIUrl":null,"url":null,"abstract":"<p><p>Organic molecules containing a difluoroalkyl group are valuable and versatile chemicals because of their unique physicochemical and biological properties. Accordingly, the development of efficient and practical difluoroalkylation for the preparation of these compounds is important and attractive. Herein, we demonstrate photoredox-catalyzed and base-dependent selective carbodifluoroalkylation and halodifluoroalkylation of alkenes using readily available 2-(allyloxy)arylaldehydes [or 2-(allylamino)arylaldehydes] and XCF<sub>2</sub>COOEt (or BrCF<sub>2</sub>CONR<sup>1</sup>R<sup>2</sup>) as starting materials. The developed reaction enables convenient and accurate synthesis of difluoroalkylated chroman-4-ones and aldehydes and features broad substrate scope, mild conditions, and operational simplicity. Moreover, gram-scale product preparation and application of the title protocol in late-stage functionalization of pharmaceutical molecules are accomplished.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01591","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/3 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Organic molecules containing a difluoroalkyl group are valuable and versatile chemicals because of their unique physicochemical and biological properties. Accordingly, the development of efficient and practical difluoroalkylation for the preparation of these compounds is important and attractive. Herein, we demonstrate photoredox-catalyzed and base-dependent selective carbodifluoroalkylation and halodifluoroalkylation of alkenes using readily available 2-(allyloxy)arylaldehydes [or 2-(allylamino)arylaldehydes] and XCF2COOEt (or BrCF2CONR1R2) as starting materials. The developed reaction enables convenient and accurate synthesis of difluoroalkylated chroman-4-ones and aldehydes and features broad substrate scope, mild conditions, and operational simplicity. Moreover, gram-scale product preparation and application of the title protocol in late-stage functionalization of pharmaceutical molecules are accomplished.
期刊介绍:
The 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.