{"title":"The Catalytic Synthesis of α-Bromo Aryl Acetic Acids by Late-Stage Bromination","authors":"Junyu Wang, Xin Wu, Beining Wang, Xiangyang Yuan, Shengnan Yang, Haipeng Hu","doi":"10.1002/ejoc.202400962","DOIUrl":null,"url":null,"abstract":"We report a catalytic late-stage bromination strategy for the α-C-H functionalization of aryl acetic acid. The aryl acetic acid was transformed into enediolate in the presence of an (AcO)4B2O with the combination of DBU, and consequently underwent an electrophilic bromination reaction with pyridinium tribromide. A wide range of α-bromo aryl acetic acids were isolated in yields of 19-65%. In addition, the reaction could be performed on a gram scale, and several transformations of the products were carried out.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.5000,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ejoc.202400962","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We report a catalytic late-stage bromination strategy for the α-C-H functionalization of aryl acetic acid. The aryl acetic acid was transformed into enediolate in the presence of an (AcO)4B2O with the combination of DBU, and consequently underwent an electrophilic bromination reaction with pyridinium tribromide. A wide range of α-bromo aryl acetic acids were isolated in yields of 19-65%. In addition, the reaction could be performed on a gram scale, and several transformations of the products were carried out.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.