{"title":"Three‐Component Synthesis of Substituted Azepines by Gold/Magnesium Orthogonal‐Relay Catalysis","authors":"Shuto Kosuge , Yoshihiro Kiraku , Kiyoshi Tsuge , Kenji Sugimoto , Yuji Matsuya","doi":"10.1002/adsc.202400940","DOIUrl":null,"url":null,"abstract":"<div><div>A three‐component one‐pot synthesis of substituted azepines was realized by gold/magnesium orthogonal relay catalysis. The one‐pot synthesis involves simply mixing and heating propiolates, imines, and activated cyclopropanes to initiate a gold‐catalyzed aza‐enyne metathesis between propiolates and imines, followed by a magnesium‐catalyzed [4+3] cycloaddition reaction of the resultant 1‐azabutadienes and the cyclopropanes, yielding substituted azepines. The substituted azepines including 22 derivatives could be successfully prepared in good to excellent yield (61–95%). The reaction was also conducted on one‐gram scale.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4674-4678"},"PeriodicalIF":4.4000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1615415024005399","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
A three‐component one‐pot synthesis of substituted azepines was realized by gold/magnesium orthogonal relay catalysis. The one‐pot synthesis involves simply mixing and heating propiolates, imines, and activated cyclopropanes to initiate a gold‐catalyzed aza‐enyne metathesis between propiolates and imines, followed by a magnesium‐catalyzed [4+3] cycloaddition reaction of the resultant 1‐azabutadienes and the cyclopropanes, yielding substituted azepines. The substituted azepines including 22 derivatives could be successfully prepared in good to excellent yield (61–95%). The reaction was also conducted on one‐gram scale.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.