{"title":"Acid/halide co-mediated transesterification of unactivated carboxylic esters with O-H nucleophiles.","authors":"Dongxu Zuo, Chenglong Li, Qiang Wu, Qun Wang, Tianzeng Huang, Long Liu, Tieqiao Chen","doi":"10.1039/d4ob02027h","DOIUrl":null,"url":null,"abstract":"<p><p>The transesterification of unactivated carboxylic esters with alcohols was achieved in one pot through acid/halide cooperative catalysis. By this strategy, various weakly nucleophilic phenols could react with unactivated methyl esters to produce the corresponding phenolic esters in good to high yields. Aliphatic alcohols could also be used as the nucleophiles and showed higher reactivity. Moreover, high functional group tolerance has been demonstrated. This reaction is also applicable to the late-stage modification of clinical drug derivatives. These results clearly show the potential synthetic value of this new reaction in organic synthesis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob02027h","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The transesterification of unactivated carboxylic esters with alcohols was achieved in one pot through acid/halide cooperative catalysis. By this strategy, various weakly nucleophilic phenols could react with unactivated methyl esters to produce the corresponding phenolic esters in good to high yields. Aliphatic alcohols could also be used as the nucleophiles and showed higher reactivity. Moreover, high functional group tolerance has been demonstrated. This reaction is also applicable to the late-stage modification of clinical drug derivatives. These results clearly show the potential synthetic value of this new reaction in organic synthesis.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
