Di Wu,Sheng Tao,Tao Wang,Jun-Yuan Tang,Fei Chen,Zhi-Hong Du,Chun-Bo Bo,Min Li,Bin Dai,Ning Liu
{"title":"α-Olefination of Nitriles: Base-Promoted Ring-Opening Coupling of Nitriles and Chromone.","authors":"Di Wu,Sheng Tao,Tao Wang,Jun-Yuan Tang,Fei Chen,Zhi-Hong Du,Chun-Bo Bo,Min Li,Bin Dai,Ning Liu","doi":"10.1021/acs.joc.5c01471","DOIUrl":null,"url":null,"abstract":"A new strategy for base-promoted ring-opening coupling reaction between nitriles and chromones for the synthesis of α-olefins was developed. This method demonstrates significant advantages, including high atomic economy, metal-free, air atmosphere, solvent-free, and room-temperature conditions. In this transformation process, the base promotes the progress of the Michael-type addition reaction, thereby initiating a ring-opening reaction between chromone and nitrile molecules. Two distinct types of α-olefination pathways for nitriles have been successfully established using a wide range of nitrile substrates. Most α-alkenylated products demonstrate notable antioxidant activity, revealing their potential applications in antioxidant development and promising prospects for pharmaceutical research.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"71 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c01471","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A new strategy for base-promoted ring-opening coupling reaction between nitriles and chromones for the synthesis of α-olefins was developed. This method demonstrates significant advantages, including high atomic economy, metal-free, air atmosphere, solvent-free, and room-temperature conditions. In this transformation process, the base promotes the progress of the Michael-type addition reaction, thereby initiating a ring-opening reaction between chromone and nitrile molecules. Two distinct types of α-olefination pathways for nitriles have been successfully established using a wide range of nitrile substrates. Most α-alkenylated products demonstrate notable antioxidant activity, revealing their potential applications in antioxidant development and promising prospects for pharmaceutical research.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.