{"title":"Substrate-Controlled Divergent Reductive Cyclization of 2-Arylanilines Using CO2 as a Switching Reagent","authors":"Qiang Yan, Jiang Nan, Rui Cao, Lanxin Zhu, Shilei Liu, Chengyuan Liang, Chen Zhang","doi":"10.1021/acs.orglett.4c04538","DOIUrl":null,"url":null,"abstract":"Capturing CO<sub>2</sub> is highly valued in the field of organic synthesis, especially underdeveloped dual-CO<sub>2</sub> conversion. In this study, we detail a novel reductive cyclization of 2-indolylanilines with dual CO<sub>2</sub> as a difunctional reagent in the presence of PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective cyclization with 2-pyrrolylanilines is also realized by converting mono-CO<sub>2</sub>. Mechanistic investigations shed light upon the fact that this substrate-controlled divergence mainly depends on the formation of <i>N</i>-diacylative intermediates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"48 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-30","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.4c04538","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
Capturing CO2 is highly valued in the field of organic synthesis, especially underdeveloped dual-CO2 conversion. In this study, we detail a novel reductive cyclization of 2-indolylanilines with dual CO2 as a difunctional reagent in the presence of PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective cyclization with 2-pyrrolylanilines is also realized by converting mono-CO2. Mechanistic investigations shed light upon the fact that this substrate-controlled divergence mainly depends on the formation of N-diacylative intermediates.
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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