Rhenium-catalyzed synthesis of indene derivatives via C-H bond activation

Yoichiro Kuninobu, Yuta Nishina, Atsushi Kawata, Makoto Shouho, Kazuhiko Takai

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Rhenium complex, [ReBr(CO)3(thf)]2-catalyzed reactions between aromatic imines and either acetylenes or α,β- unsaturated carbonyl compounds gave indene derivatives in good to excellent yields. These reactions proceed via C-H bond activation, insertion of acetylenes or α,β-unsaturated carbonyl compounds, intramolecular nucleophilic cyclization, and reductive elimination. Indene derivatives were also obtained from aromatic ketones and α,β-unsaturated carbonyl compounds in the presence of catalytic amounts of the rhenium complex and p-anisidine. Sequential ruthenium-catalyzed hydroamination of aromatic acetylenes with anilines, and rhenium-catalyzed reactions of the formed aromatic ketimines with α,β-unsaturated carbonyl compounds also provided indene derivatives.

Original languageEnglish
Pages (from-to)1149-1154
Number of pages6
JournalPure and Applied Chemistry
Volume80
Issue number5
DOIs
Publication statusPublished - May 2008

Fingerprint

Rhenium
Carbonyl compounds
Alkynes
Acetylene
Chemical activation
Derivatives
Aniline Compounds
Imines
Ruthenium
Cyclization
Carbon Monoxide
Aniline
Ketones
indene

Keywords

  • Atom-economical
  • C-H activation
  • Indene
  • Rhenium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Rhenium-catalyzed synthesis of indene derivatives via C-H bond activation. / Kuninobu, Yoichiro; Nishina, Yuta; Kawata, Atsushi; Shouho, Makoto; Takai, Kazuhiko.

In: Pure and Applied Chemistry, Vol. 80, No. 5, 05.2008, p. 1149-1154.

Research output: Contribution to journalArticle

Kuninobu, Yoichiro ; Nishina, Yuta ; Kawata, Atsushi ; Shouho, Makoto ; Takai, Kazuhiko. / Rhenium-catalyzed synthesis of indene derivatives via C-H bond activation. In: Pure and Applied Chemistry. 2008 ; Vol. 80, No. 5. pp. 1149-1154.
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