{"title":"A Reductive Ugi Reaction with Carboxylic Acids Replacing Aldehydes.","authors":"Xiaohong Li,Jinxi Huang,Huanfeng Jiang,Liangbin Huang","doi":"10.1021/acs.orglett.5c01785","DOIUrl":null,"url":null,"abstract":"Here, we report a Ti(IV)-catalyzed reductive Ugi reaction in which two distinct carboxylic acids replace aldehyde and carboxylic acid components. The Ti(IV) catalyst exhibits dual roles: promoting the deoxygenative imination of carboxylic acids through its oxophilicity and acting as a Lewis acid to activate imine intermediates for the the Ugi reaction. The addition of methanol quenches excess hydrosilane, ensuring an efficient tandem process. This one-pot tandem reaction expands the carboxylic acid utility in MCRs, offering a platform for drug discovery, functional materials, and natural product synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"142 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-05-26","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.5c01785","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
Here, we report a Ti(IV)-catalyzed reductive Ugi reaction in which two distinct carboxylic acids replace aldehyde and carboxylic acid components. The Ti(IV) catalyst exhibits dual roles: promoting the deoxygenative imination of carboxylic acids through its oxophilicity and acting as a Lewis acid to activate imine intermediates for the the Ugi reaction. The addition of methanol quenches excess hydrosilane, ensuring an efficient tandem process. This one-pot tandem reaction expands the carboxylic acid utility in MCRs, offering a platform for drug discovery, functional materials, and natural product synthesis.
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.