{"title":"Visible light-promoted defluorinative alkylation/arylation of α-trifluoromethyl alkenes with thianthrenium salts†","authors":"","doi":"10.1039/d4gc02901a","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, an operationally simple and mild protocol for defluorinative alkylation and arylation between thianthrenium salts and α-trifluoromethyl alkene with visible light to afford <em>gem</em>-difluoroolefins has been developed. The main feature of this method is avoiding the use of a metal photocatalyst, and an organic photocatalyst is unnecessary for the arylation reaction. In addition, thianthrene can also be recycled and transformed to thianthrenium salts without affecting the efficiency of these reactions. The protocol demonstrates excellent tolerance of functional groups and viable functionalization of late-stage natural products and pharmaceutically relevant molecules.</p></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.3000,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1463926224007064","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, an operationally simple and mild protocol for defluorinative alkylation and arylation between thianthrenium salts and α-trifluoromethyl alkene with visible light to afford gem-difluoroolefins has been developed. The main feature of this method is avoiding the use of a metal photocatalyst, and an organic photocatalyst is unnecessary for the arylation reaction. In addition, thianthrene can also be recycled and transformed to thianthrenium salts without affecting the efficiency of these reactions. The protocol demonstrates excellent tolerance of functional groups and viable functionalization of late-stage natural products and pharmaceutically relevant molecules.
期刊介绍:
Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.