Ang Gao , He-Xiang Liu , Ya-Nan Zhou , Ming-Chen Fu
{"title":"A catalyst- and thiol-free protocol for arene C–H thioetherification via photoactive electron donor–acceptor complexes†","authors":"Ang Gao , He-Xiang Liu , Ya-Nan Zhou , Ming-Chen Fu","doi":"10.1039/d4gc06257d","DOIUrl":null,"url":null,"abstract":"<div><div>We present a catalyst- and thiol-free protocol for arene C–H thioetherification under visible light irradiation, yielding a diverse array of aryl alkyl thioethers, including <em>d</em><sub>3</sub>-methyl aryl thioethers. A key discovery is that tetramethylthiourea can serve as both a sulfur source and an electron donor, facilitating the formation of the EDA complex with arylsulfonium salts. The method's effectiveness in gram-scale synthesis and adaptability for continuous flow processes underscore its significant synthetic potential and versatility.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 8","pages":"Pages 2286-2292"},"PeriodicalIF":9.3000,"publicationDate":"2025-01-21","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/S1463926225000603","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
We present a catalyst- and thiol-free protocol for arene C–H thioetherification under visible light irradiation, yielding a diverse array of aryl alkyl thioethers, including d3-methyl aryl thioethers. A key discovery is that tetramethylthiourea can serve as both a sulfur source and an electron donor, facilitating the formation of the EDA complex with arylsulfonium salts. The method's effectiveness in gram-scale synthesis and adaptability for continuous flow processes underscore its significant synthetic potential and versatility.
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.