Xiang Liu , Jiawei He , Keyu Lin , Xingyue Wang , Hua Cao
{"title":"State-of-the-art strategies for Lewis acid-catalyzed strain-release cycloadditions of bicyclo[1.1.0]butanes (BCBs)","authors":"Xiang Liu , Jiawei He , Keyu Lin , Xingyue Wang , Hua Cao","doi":"10.1039/d4qo01741b","DOIUrl":null,"url":null,"abstract":"<div><div>Due to their low activation energy barriers, small strained carbocyclic systems have always been fascinating building blocks in organic chemistry. Among them, BCBs, as the smallest bicyclic carbocycles, exhibit a molecular structure, bond angles, and orbital hybridization significantly different from those of strain-free hydrocarbons, resulting in unique reactivity. In recent years, Lewis acid-catalyzed strain-release cycloaddition reactions have made BCBs powerful synthetic tools, utilized in various laboratories to expand into other ring systems. This review primarily focuses on the latest developments in Lewis acid-catalyzed strain-release cycloaddition reactions of BCBs, highlighting the applications and limitations of this catalytic system in different types of cycloaddition reactions, providing professionals and non-professionals in the field with valuable insights and new inspiration.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 23","pages":"Pages 6942-6957"},"PeriodicalIF":0.0000,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S205241292400737X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Due to their low activation energy barriers, small strained carbocyclic systems have always been fascinating building blocks in organic chemistry. Among them, BCBs, as the smallest bicyclic carbocycles, exhibit a molecular structure, bond angles, and orbital hybridization significantly different from those of strain-free hydrocarbons, resulting in unique reactivity. In recent years, Lewis acid-catalyzed strain-release cycloaddition reactions have made BCBs powerful synthetic tools, utilized in various laboratories to expand into other ring systems. This review primarily focuses on the latest developments in Lewis acid-catalyzed strain-release cycloaddition reactions of BCBs, highlighting the applications and limitations of this catalytic system in different types of cycloaddition reactions, providing professionals and non-professionals in the field with valuable insights and new inspiration.