Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie
{"title":"Catalyst-controlled switchable formal retro-Büchner reaction for the divergent synthesis of benzo[b]azepines and 1, 3-conjugated dienes","authors":"Zhaoxue Wang , Menghui Guo , Ping Wu , Rui Yan , Guili Zhao , Ming Liu , Yilei Xiao , Lingang Wu , Lei Xie","doi":"10.1016/j.tet.2024.134378","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with <em>N</em>-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[<em>b</em>]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134378"},"PeriodicalIF":2.1000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024005593","RegionNum":3,"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
Herein, a phosphine catalyst-controlled switchable formal retro-Büchner reaction of MBH carbonates with N-sulfonyl azaheptafulvenes has been successfully developed, which provides a divergent and efficient route to access valuable benzo[b]azepine and multiple substituted 1, 3-conjugated diene derivatives in moderate to great yields. Additionally, these methodologies are characterized by mild reaction conditions, absence of transition metal, easy operation, broad functional-group tolerance, and amenability to gram-scale synthesis.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.