Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel- Crafts reaction of arylidenecyclopropanes with acetals

Itaru Nakamura, Michiru Kamada, Yoshinori Yamamoto

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31 Citations (Scopus)

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 10mol% 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.

Original languageEnglish
Pages (from-to)2903-2906
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number14
DOIs
Publication statusPublished - 2004 Mar 29

Keywords

  • Carboalkoxylation
  • Friedel-Craft reaction
  • Indene
  • Lewis acid catalysis
  • Ytterbium catalyzed reaction
  • Ytterbium triflate
  • exo-Methylenecyclopropane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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