{"title":"Selective C–O bond cleavage at benzylic positions enabled by Zirconocene and Photoredox catalysis","authors":"Kazuhiro Aida , Ryota Tajima , Eisuke Ota , Junichiro Yamaguchi","doi":"10.1016/j.tetlet.2025.155741","DOIUrl":null,"url":null,"abstract":"<div><div>We have developed a catalytic protocol for the selective cleavage of C–O bonds at benzylic positions using zirconocene and photoredox catalysis. This catalytic system enables the reductive cleavage of C–O bonds in both benzyl ethers and benzyl alcohols. Additionally, aromatic carbonyl compounds undergo deoxygenation to afford the corresponding hydrogenated products. Mechanistic studies support that ZrIII is the catalytically active species responsible for the C–O bond cleavage, driven by the formation of a strong Zr–O bond.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155741"},"PeriodicalIF":1.5000,"publicationDate":"2025-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925002904","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We have developed a catalytic protocol for the selective cleavage of C–O bonds at benzylic positions using zirconocene and photoredox catalysis. This catalytic system enables the reductive cleavage of C–O bonds in both benzyl ethers and benzyl alcohols. Additionally, aromatic carbonyl compounds undergo deoxygenation to afford the corresponding hydrogenated products. Mechanistic studies support that ZrIII is the catalytically active species responsible for the C–O bond cleavage, driven by the formation of a strong Zr–O bond.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.