{"title":"Rhodium-Catalyzed C–H Heteroarylation and Alkenylation of N-Phenoxyacetamides Using Iodonium Ylides","authors":"Wenqian Ding, , , Wanqi Hu, , , Weiqi Liu, , and , Xiaowei Wu*, ","doi":"10.1021/acs.joc.5c00858","DOIUrl":null,"url":null,"abstract":"<p >Herein, we describe a rhodium-catalyzed monoheteroarylation and alkenylation of <i>N-</i>phenoxyacetamides using iodonium ylides derived from cyclo-1,3-diones. This approach efficiently delivers novel heteroarylated and alkenylated products under mild reaction conditions. The protocol showcases good functional group tolerance and a wide substrate scope. Furthermore, this allows for smooth scale-up synthesis. Additional transformation experiments were conducted to highlight the potential synthetic utility of this methodology.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 41","pages":"14373–14382"},"PeriodicalIF":3.6000,"publicationDate":"2025-10-06","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://pubs.acs.org/doi/10.1021/acs.joc.5c00858","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
Herein, we describe a rhodium-catalyzed monoheteroarylation and alkenylation of N-phenoxyacetamides using iodonium ylides derived from cyclo-1,3-diones. This approach efficiently delivers novel heteroarylated and alkenylated products under mild reaction conditions. The protocol showcases good functional group tolerance and a wide substrate scope. Furthermore, this allows for smooth scale-up synthesis. Additional transformation experiments were conducted to highlight the potential synthetic utility of this methodology.
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.