Ruoyu Zhang, Qingqing Wu, Xiuzhe Xie, Jingjing Zhao, Yun Chai, Bingchuan Yang, Puyu Zhang, Pan Li
{"title":"Palladium-Catalyzed [4 + 1] Annulation of Benzofuran-Derived Azadienes with Isocyanides","authors":"Ruoyu Zhang, Qingqing Wu, Xiuzhe Xie, Jingjing Zhao, Yun Chai, Bingchuan Yang, Puyu Zhang, Pan Li","doi":"10.1021/acs.joc.5c00769","DOIUrl":null,"url":null,"abstract":"A palladium-catalyzed [4 + 1] annulation of benzofuran-derived azadienes and isocyanides has been developed. This protocol provides an efficient and practical approach to obtain diverse benzofuro[3,2-<i>b</i>]pyrrole derivatives in moderate to good yields. The reaction appears to proceed through Pd<sup>II</sup>-assisted intramolecular Michael addition, followed by 5-<i>exo-dig</i> cyclization, aromatization, and subsequent base-assisted desulfonylation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"18 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-06-07","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.5c00769","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 palladium-catalyzed [4 + 1] annulation of benzofuran-derived azadienes and isocyanides has been developed. This protocol provides an efficient and practical approach to obtain diverse benzofuro[3,2-b]pyrrole derivatives in moderate to good yields. The reaction appears to proceed through PdII-assisted intramolecular Michael addition, followed by 5-exo-dig cyclization, aromatization, and subsequent base-assisted desulfonylation.
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.