Rhenium-catalyzed synthesis of indenones by novel dehydrative trimerization of aryl aldehydes via C-H bond activation

Yoichiro Kuninobu, Takashi Matsuki, Kazuhiko Takai

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By heating aryl aldehydes with catalytic amounts of a rhenium complex, ReBr(CO)5, and N-phenylacetamide in toluene, indenone derivatives are obtained in good to excellent yields. This reaction proceeds via (1) the formation of an isobenzofuran derivative by the insertion of an aldehyde into the C-H bond of another aldehyde (C-H bond activation) and successive intramolecular nucleophilic cyclization, (2) nucleophilic addition of the formed isobenzofuran derivative to the third aldehyde, (3) isomerization, and (4) intramolecular aldol condensation.

Original languageEnglish
Pages (from-to)2948-2950
Number of pages3
JournalOrganic Letters
Issue number13
Publication statusPublished - Jul 2 2010


ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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