Dr. Karen J. Ardila-Fierro, Leonarda Vugrin, Dr. Ivan Halasz, Dr. Ana Palčić, Prof. José G. Hernández
{"title":"Mechanochemical Bromination of Naphthalene Catalyzed by Zeolites: From Small Scale to Continuous Synthesis","authors":"Dr. Karen J. Ardila-Fierro, Leonarda Vugrin, Dr. Ivan Halasz, Dr. Ana Palčić, Prof. José G. Hernández","doi":"10.1002/cmtd.202200035","DOIUrl":null,"url":null,"abstract":"<p>Catalyzed reactions of organic substrates that operate continuously by extrusion techniques are rare. In this study, we developed a mechanochemical bromination of unactivated naphthalene (<b>1</b>) with 1,3-dibromo-5,5-dimethylhydantoin (<b>DBDMH</b>), catalyzed by zeolites in a ball mill. The use of <b>DBDMH</b> enabled the atom economy of the reaction to be superior compared to the other brominating agents evaluated. Among the zeolites tested, a FAU-type zeolite demonstrated high catalytic activity and recyclability. The success of the bromination route on a small scale enabled the development of a continuous catalyzed bromination of <b>1</b> by twin-screw extrusion.</p>","PeriodicalId":72562,"journal":{"name":"Chemistry methods : new approaches to solving problems in chemistry","volume":null,"pages":null},"PeriodicalIF":6.1000,"publicationDate":"2022-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cmtd.202200035","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry methods : new approaches to solving problems in chemistry","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cmtd.202200035","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Catalyzed reactions of organic substrates that operate continuously by extrusion techniques are rare. In this study, we developed a mechanochemical bromination of unactivated naphthalene (1) with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), catalyzed by zeolites in a ball mill. The use of DBDMH enabled the atom economy of the reaction to be superior compared to the other brominating agents evaluated. Among the zeolites tested, a FAU-type zeolite demonstrated high catalytic activity and recyclability. The success of the bromination route on a small scale enabled the development of a continuous catalyzed bromination of 1 by twin-screw extrusion.