Dong-Sheng Ji, Chenxing Zhou, Xin Zhang, Youwan Ye, Xiazhen Bao, Yong Yuan, Congde Huo
{"title":"Photoredox/NHC Dual Catalysis Enabled de Novo Synthesis of α-Amino Acids Derivatives.","authors":"Dong-Sheng Ji, Chenxing Zhou, Xin Zhang, Youwan Ye, Xiazhen Bao, Yong Yuan, Congde Huo","doi":"10.1021/acs.orglett.4c03387","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we report a mild and operationally simple photoredox/NHC dual catalysis strategy for the α-carboxylation of tertiary amine C(sp<sup>3</sup>)-H bonds using diethyl pyrocarbonate. This method offers a novel approach for synthesizing α-amino acid derivatives. The protocol features a broad substrate scope, accommodating both N-aryl tetrahydroisoquinolines (THIQ) and <i>N</i>-methyl aniline and is scalable to gram quantities. Additionally, it is suitable for the late-stage derivatization of certain pharmaceutical compounds.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-04","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.4c03387","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/23 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report a mild and operationally simple photoredox/NHC dual catalysis strategy for the α-carboxylation of tertiary amine C(sp3)-H bonds using diethyl pyrocarbonate. This method offers a novel approach for synthesizing α-amino acid derivatives. The protocol features a broad substrate scope, accommodating both N-aryl tetrahydroisoquinolines (THIQ) and N-methyl aniline and is scalable to gram quantities. Additionally, it is suitable for the late-stage derivatization of certain pharmaceutical compounds.
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.