Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

Daichi Kawauchi, Kenta Noda, Yoshiyuki Komatsu, Kei Yoshida, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

Original languageEnglish
Pages (from-to)15793-15798
Number of pages6
JournalChemistry - A European Journal
Volume26
Issue number68
DOIs
Publication statusPublished - 2020 Dec 4

Keywords

  • Grubbs catalyst
  • aerobic oxidation
  • dehydrogenation
  • heterocycle
  • tandem catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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