Caicai He , Swastik Karmakar , Dandan Wei , Wei Zhao , Xiaolong Zhang , Xihe Bi
{"title":"Rh-catalyzed asymmetric cyclopropanation of benzofurans with trifluoromethyl N-triftosylhydrazones","authors":"Caicai He , Swastik Karmakar , Dandan Wei , Wei Zhao , Xiaolong Zhang , Xihe Bi","doi":"10.1016/j.jfluchem.2023.110237","DOIUrl":null,"url":null,"abstract":"<div><p>An asymmetric dearomative cyclopropanation of benzofuran has been accomplished by a novel catalytic method that relies on using trifluoromethyl <em>N</em>-triftosylhydrazones as carbene sources in the presence of a chiral rhodium catalyst. This reaction produces chiral trifluoromethyl-tethered 2,3-disubstituted benzofuran cyclopropane, which carries versatile pharmacophores 2,3-dihydrobenzofuran and trifluoromethyl-substituted quaternary carbon centers. Notably, this process offers distinct advantages over other existing approaches due to being step-economic and eliminating green-gas N<sub>2</sub> as a harmless coproduct. DFT calculations explain the reason behind the high enantioselectivity during this cyclopropanation reaction.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113923001525/pdfft?md5=80519f4aba46016beb0c02ac04463280&pid=1-s2.0-S0022113923001525-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Fluorine Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022113923001525","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
An asymmetric dearomative cyclopropanation of benzofuran has been accomplished by a novel catalytic method that relies on using trifluoromethyl N-triftosylhydrazones as carbene sources in the presence of a chiral rhodium catalyst. This reaction produces chiral trifluoromethyl-tethered 2,3-disubstituted benzofuran cyclopropane, which carries versatile pharmacophores 2,3-dihydrobenzofuran and trifluoromethyl-substituted quaternary carbon centers. Notably, this process offers distinct advantages over other existing approaches due to being step-economic and eliminating green-gas N2 as a harmless coproduct. DFT calculations explain the reason behind the high enantioselectivity during this cyclopropanation reaction.
期刊介绍：
The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature.
For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
