{"title":"Arylation of ortho-Hydroxyarylenaminones by Sulfonium Salts and Arenesulfonyl Chlorides: An Access to Isoflavones","authors":"Satenik Mkrtchyan*, Viktor O. Iaroshenko*","doi":"10.1021/acs.joc.0c02294","DOIUrl":null,"url":null,"abstract":"<p >Herein we disclose three new methods for the straightforward and efficient synthesis of 3-arylchromones following the arylation of <i>ortho</i>-hydroxyarylenaminones by vast diversities of bench-stable and easy-to-use sulfonium salts and arenesulfonyl chlorides. Both developed methods, namely the light-mediated photoredox and electrophilic arylation, showed good efficiency, and are feasible for the preparation of 3-arylchromones in good-to-excellent yields. This work showcases the first described attempt where the sulfonium salts and arenesulfonyl chlorides were successfully utilized for the construction of the chromone heterocycle system.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"86 7","pages":"4896–4916"},"PeriodicalIF":3.6000,"publicationDate":"2021-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1021/acs.joc.0c02294","citationCount":"9","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.0c02294","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: 9
Abstract
Herein we disclose three new methods for the straightforward and efficient synthesis of 3-arylchromones following the arylation of ortho-hydroxyarylenaminones by vast diversities of bench-stable and easy-to-use sulfonium salts and arenesulfonyl chlorides. Both developed methods, namely the light-mediated photoredox and electrophilic arylation, showed good efficiency, and are feasible for the preparation of 3-arylchromones in good-to-excellent yields. This work showcases the first described attempt where the sulfonium salts and arenesulfonyl chlorides were successfully utilized for the construction of the chromone heterocycle system.
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.