{"title":"NHC/Pd Synergistically Catalyzed Direct Aerobic Oxidative Allylic Esterification of Aldehydes.","authors":"Chhanda Debnath,Shikha Gandhi","doi":"10.1021/acs.orglett.5c01392","DOIUrl":null,"url":null,"abstract":"N-Heterocyclic carbene (NHC)-mediated aerobic oxidation of aldehydes has gained interest in recent years. However, its application in NHC/Pd synergistic catalysis has been unexplored. We have developed a strategy to synthesize allylic esters directly from aldehydes and Morita-Baylis-Hillman (MBH) carbonates using NHC/Pd synergistic (cooperative) catalysis under aerobic conditions. This transformation gives access to the selective formation of multifunctionalized E-alkenes by β-attack on the MBH carbonates. This catalytic system also allows the use of water as a cosolvent and air as the sole green oxidant.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"17 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c01392","RegionNum":1,"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
N-Heterocyclic carbene (NHC)-mediated aerobic oxidation of aldehydes has gained interest in recent years. However, its application in NHC/Pd synergistic catalysis has been unexplored. We have developed a strategy to synthesize allylic esters directly from aldehydes and Morita-Baylis-Hillman (MBH) carbonates using NHC/Pd synergistic (cooperative) catalysis under aerobic conditions. This transformation gives access to the selective formation of multifunctionalized E-alkenes by β-attack on the MBH carbonates. This catalytic system also allows the use of water as a cosolvent and air as the sole green oxidant.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.