{"title":"Solvent-controlled catalytic divergent C–H alkylation of quinolones driven by unusual DMSO-promoted 1,3-heteroarene migration","authors":"Ye Lim Kim, Yuri Yun, Seoung-Mi Choi, Ju Hyun Kim","doi":"10.1039/d4qo01980f","DOIUrl":null,"url":null,"abstract":"We report on a catalytic divergent C–H alkylation of 4-quinolones with diazo compounds where the reaction pathways are controlled by a reaction solvent. Cp*Rh(III)-catalyzed site-selective C−H alkylation was carried out in dichloromethane to produce C2-alkylated 4-quinolones. C(2)−H alkylation and sequential [1,3]-heteroarene rearrangement were achieved by utilizing EtOH/DMSO solvent in the same catalytic system at 70°C, allowing valuable 4-quinolones bearing an all-carbon quaternary center at the 2-position to be efficiently synthesized in a one-pot operation. By combining experimental results and computational studies, we propose an unprecedented DMSO-promoted Truce-Smiles rearrangement.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"63 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-12-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01980f","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
We report on a catalytic divergent C–H alkylation of 4-quinolones with diazo compounds where the reaction pathways are controlled by a reaction solvent. Cp*Rh(III)-catalyzed site-selective C−H alkylation was carried out in dichloromethane to produce C2-alkylated 4-quinolones. C(2)−H alkylation and sequential [1,3]-heteroarene rearrangement were achieved by utilizing EtOH/DMSO solvent in the same catalytic system at 70°C, allowing valuable 4-quinolones bearing an all-carbon quaternary center at the 2-position to be efficiently synthesized in a one-pot operation. By combining experimental results and computational studies, we propose an unprecedented DMSO-promoted Truce-Smiles rearrangement.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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