Rh-catalyzed asymmetric cyclopropanation of benzofurans with trifluoromethyl N-triftosylhydrazones

IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Fluorine Chemistry Pub Date : 2024-01-01 DOI:10.1016/j.jfluchem.2023.110237
Caicai He , Swastik Karmakar , Dandan Wei , Wei Zhao , Xiaolong Zhang , Xihe Bi
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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.

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Rh 催化的苯并呋喃与三氟甲基 N-三十烷基肼的不对称环丙烷化反应
通过一种新颖的催化方法,在手性铑催化剂存在下,使用三氟甲基 N-三十烷基肼作为碳源,完成了苯并呋喃的不对称脱芳香环丙烷化反应。该反应生成了手性三氟甲基拴系的 2,3-二取代苯并呋喃环丙烷,该环丙烷带有 2,3-二氢苯并呋喃和三氟甲基取代的季碳中心。值得注意的是,与其他现有方法相比,这一工艺具有明显的优势,因为它具有分步经济性,而且消除了作为无害副产物的绿色气体 N2。DFT 计算解释了该环丙烷化反应具有高对映体选择性的原因。
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来源期刊
Journal of Fluorine Chemistry
Journal of Fluorine Chemistry 化学-无机化学与核化学
CiteScore
3.80
自引率
10.50%
发文量
99
审稿时长
33 days
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.
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