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

Yoichiro Kuninobu, Takashi Matsuki, Kazuhiko Takai

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

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
Volume12
Issue number13
DOIs
Publication statusPublished - Jul 2 2010

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Rhenium
rhenium
aldehydes
Aldehydes
Chemical activation
activation
synthesis
Derivatives
Cyclization
Toluene
Carbon Monoxide
Isomerization
Heating
isomerization
toluene
insertion
Condensation
condensation
heating

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Rhenium-catalyzed synthesis of indenones by novel dehydrative trimerization of aryl aldehydes via C-H bond activation. / Kuninobu, Yoichiro; Matsuki, Takashi; Takai, Kazuhiko.

In: Organic Letters, Vol. 12, No. 13, 02.07.2010, p. 2948-2950.

Research output: Contribution to journalArticle

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