Zhaoyang Zhang , Jia-Yi Yang , Shihao Li , Xiao-Xuan Li , Yi-Si Feng
{"title":"NHC and photoredox co-catalyzed 1,4-alkylcarbonylation of 1,3-enynes†","authors":"Zhaoyang Zhang , Jia-Yi Yang , Shihao Li , Xiao-Xuan Li , Yi-Si Feng","doi":"10.1039/d4qo02311k","DOIUrl":null,"url":null,"abstract":"<div><div>A strategy to obtain 1,2-alkenyl ketone products by radical relay coupling is proposed. We report that the ketyl radical produced by the single electron reduction of acyl azolium mediated by NHCs is a good coupling partner of alkenyl radicals, and the imidazole ions generated in this process directly activate alkylboronic acids to form alkyl radicals. This transformation mode is carried out under mild conditions and shows an excellent range of substrate applications.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 3984-3989"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412925002372","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/4/3 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A strategy to obtain 1,2-alkenyl ketone products by radical relay coupling is proposed. We report that the ketyl radical produced by the single electron reduction of acyl azolium mediated by NHCs is a good coupling partner of alkenyl radicals, and the imidazole ions generated in this process directly activate alkylboronic acids to form alkyl radicals. This transformation mode is carried out under mild conditions and shows an excellent range of substrate applications.
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