Alexandre Simon , Virgile Rouffeteau , Camilla Acconcia , Sylvestre P. J. T. Bachollet , Jérémy Forté , Mariateresa Giustiniano , Laurence Grimaud , Maxime R. Vitale
{"title":"Pseudo-4-component photoredox-catalyzed alkylative amidination/carbamoylation of styrenes with isocyanides and redox-active esters†","authors":"Alexandre Simon , Virgile Rouffeteau , Camilla Acconcia , Sylvestre P. J. T. Bachollet , Jérémy Forté , Mariateresa Giustiniano , Laurence Grimaud , Maxime R. Vitale","doi":"10.1039/d5qo00352k","DOIUrl":null,"url":null,"abstract":"<div><div>We report a photoredox-catalyzed pseudo-four-component process for the alkylative amidination of styrenes using isocyanides and redox-active esters (RAEs). This redox-neutral radical-polar crossover reaction shows broad functional group tolerance. The RAE serves as both a radical and nucleophile source, with the initially released phthalimide anion reintegrated into the final product. The resulting amidines can be readily derivatized into amides, tetrazoles, nitriles, or aldehydes, enhancing the synthetic utility of this approach.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 12","pages":"Pages 3551-3557"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-03","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/S2052412925001913","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
We report a photoredox-catalyzed pseudo-four-component process for the alkylative amidination of styrenes using isocyanides and redox-active esters (RAEs). This redox-neutral radical-polar crossover reaction shows broad functional group tolerance. The RAE serves as both a radical and nucleophile source, with the initially released phthalimide anion reintegrated into the final product. The resulting amidines can be readily derivatized into amides, tetrazoles, nitriles, or aldehydes, enhancing the synthetic utility of this approach.