Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes with acetals |
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Authors: | Itaru Nakamura |
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Affiliation: | Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki Aza Aoba, Sendai 980-8578, Japan |
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Abstract: | Ytterbium-catalyzed tandem carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes 1 with acetals 2 afforded the corresponding indene derivatives 3 in good to high yields. For example, in the presence of 10 mol % of Yb(OTf)3 the reaction of 1-phenylbenzylidenecyclopropane 1a with the dimethyl acetals of benzaldehyde 2a, p-tolualdehyde 2b, and p-anisaldehyde 2c gave 1,3-diphenyl-2-(2-methoxyethyl)indene 3a, 2-(2-methoxyethyl)-3-phenyl-1-(p-tolyl)indene 3b, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene 3c in 82%, 80%, and 80% yields, respectively. |
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Keywords: | Indene Lewis acid catalysis Ytterbium triflate exo-Methylenecyclopropane Carboalkoxylation Friedel-Craft reaction Ytterbium catalyzed reaction |
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