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 journalArticlepeer-review

245 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

All Science Journal Classification (ASJC) codes

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

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