Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation: Synthesis of phthalimidine and indene derivatives

Yoichiro Kuninobu, Yukimi Tokunaga, Atsushi Kawata, Kazuhiko Takai

Research output: Contribution to journalArticle

238 Citations (Scopus)

Abstract

A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of an aromatic aldimine with an isocyanate and an acetylene to give a phthalimidine and an indene derivative in a quantitative yield, respectively. The reactions proceed via C-H bond activation, insertion of the isocyanate or the acetylene, Intramolecular nucleophilic cyclization to the aldimine of the generated amido- or alkenyl-rhenium species, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the insertion of a polar unsaturated molecule. This occurs more easily than the insertion of a nonpolar unsaturated molecule.

Original languageEnglish
Pages (from-to)202-209
Number of pages8
JournalJournal of the American Chemical Society
Volume128
Issue number1
DOIs
Publication statusPublished - Jan 11 2006
Externally publishedYes

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Rhenium
Isocyanates
Acetylene
Carbon
Chemical activation
Derivatives
Molecules
Rhodium
Catalysts
Ruthenium
Cyclization
Carbon Monoxide
phthalimidine
indene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation : Synthesis of phthalimidine and indene derivatives. / Kuninobu, Yoichiro; Tokunaga, Yukimi; Kawata, Atsushi; Takai, Kazuhiko.

In: Journal of the American Chemical Society, Vol. 128, No. 1, 11.01.2006, p. 202-209.

Research output: Contribution to journalArticle

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