{"title":"Synthesis of Multisubstituted Arylnitriles via Tf2O-Mediated Benzannulation of Enaminones with Acylacetonitriles","authors":"Xiaohan Zhang, Fei Li, Yue Zhou, Junxian Zhang, Benwei Zhou, Lulu Chen, Jianping Lin, Changyuan Zhang","doi":"10.1021/acs.orglett.5c00261","DOIUrl":null,"url":null,"abstract":"A novel and efficient method for the synthesis of multisubstituted arylnitriles <i>via</i> Tf<sub>2</sub>O-mediated [3 + 2 + 1] benzannulation of enaminones and acylacetonitriles has been developed. This reaction proceeds under mild conditions with excellent functional group compatibility. Mechanistic studies have revealed that the cyclization involves two consecutive nucleophilic additions, followed by a cascade Knoevenagel condensation and aromatization. Additionally, trifluoromethanesulfonate <b>6</b> has been identified as a crucial intermediate in this process.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"40 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00261","RegionNum":1,"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 novel and efficient method for the synthesis of multisubstituted arylnitriles via Tf2O-mediated [3 + 2 + 1] benzannulation of enaminones and acylacetonitriles has been developed. This reaction proceeds under mild conditions with excellent functional group compatibility. Mechanistic studies have revealed that the cyclization involves two consecutive nucleophilic additions, followed by a cascade Knoevenagel condensation and aromatization. Additionally, trifluoromethanesulfonate 6 has been identified as a crucial intermediate in this process.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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