{"title":"Ruthenium-Catalyzed Decarboxylative Direct 2-Pyridination of α,β-Unsaturated Carboxylic Acids.","authors":"Jiaojiao Guo,Ying Zhu,Jing Zhang","doi":"10.1021/acs.joc.5c00375","DOIUrl":null,"url":null,"abstract":"We report a ruthenium-catalyzed decarboxylative direct mono-2-pyridination of α,β-unsaturated carboxylic acids, offering a selective method for synthesizing 2-(1-arylalkenyl)pyridines. Under redox-neutral conditions, the reaction demonstrates broad substrate scope, high functional group tolerance, and significant potential for further derivatization. Mechanistic studies reveal that selective activation of the allylic C(sp3)-H bond, directed by the pyridine group, underpins the observed mono-2-pyridination. This work provides an efficient and selective strategy for the catalytic decarboxylative transformation of α,β-unsaturated carboxylic acids, expanding the toolbox for functionalizing pyridine derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-05-19","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.5c00375","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
We report a ruthenium-catalyzed decarboxylative direct mono-2-pyridination of α,β-unsaturated carboxylic acids, offering a selective method for synthesizing 2-(1-arylalkenyl)pyridines. Under redox-neutral conditions, the reaction demonstrates broad substrate scope, high functional group tolerance, and significant potential for further derivatization. Mechanistic studies reveal that selective activation of the allylic C(sp3)-H bond, directed by the pyridine group, underpins the observed mono-2-pyridination. This work provides an efficient and selective strategy for the catalytic decarboxylative transformation of α,β-unsaturated carboxylic acids, expanding the toolbox for functionalizing pyridine derivatives.
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.