Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines
{"title":"Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines","authors":"Peipei Ma, Hongli Wu, H. Gan","doi":"10.1055/a-2160-8903","DOIUrl":null,"url":null,"abstract":"A visible-light-mediated metal-free oxidation of 1-BnDHIQs to switchable preparation of BzIQs and BzDHIQs has been realized in which dioxygen as an oxidant. 6,7-Dialkoxy BzIQs and BzDHIQs were comprehensively synthesized in this protocol. This protocol provides a facile route for the efficient synthesis of isoquinoline alkaloids. Mechanistic investigation suggested that radical pathway and ionic pathway may exist simultaneously and intermediate A may be the key compound for the formation of the products.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"1 1","pages":""},"PeriodicalIF":2.2000,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis-Stuttgart","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-2160-8903","RegionNum":4,"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
A visible-light-mediated metal-free oxidation of 1-BnDHIQs to switchable preparation of BzIQs and BzDHIQs has been realized in which dioxygen as an oxidant. 6,7-Dialkoxy BzIQs and BzDHIQs were comprehensively synthesized in this protocol. This protocol provides a facile route for the efficient synthesis of isoquinoline alkaloids. Mechanistic investigation suggested that radical pathway and ionic pathway may exist simultaneously and intermediate A may be the key compound for the formation of the products.
期刊介绍:
SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.