Feifei Jin, Qing Wu, Shuaijie Wu, Huiwen Dong, Yanru He, Jing Sun, Chao-Guo Yan, Wenbo Li, Lei Wang
{"title":"Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs","authors":"Feifei Jin, Qing Wu, Shuaijie Wu, Huiwen Dong, Yanru He, Jing Sun, Chao-Guo Yan, Wenbo Li, Lei Wang","doi":"10.1021/acs.joc.4c02679","DOIUrl":null,"url":null,"abstract":"A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2024-12-18","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.4c02679","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 novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.
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.