A modular synthesis of 1,4,5-trisubstituted 1,2,3-triazoles with ferrocene moieties

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Abstract

Abstract Regioselective synthesis of 1,2,3-triazoles with ferrocenyl moieties in positions 1, 4, and 5 was carried out in a two-step reaction sequence: a copper-mediated azide-alkyne cycloaddition followed by a palladium-catalyzed cross-coupling. A new route towards 5-iodo-1,2,3-triazoles was developed using N-iodomorpholine hydrogen iodide, instead of the corrosive and toxic ICl, as the I+ source. The novel methodology together with a consecutive Suzuki or Sonogashira reaction was shown to be a useful procedure for the synthesis of a wide range of ferrocenyl 1,2,3-triazoles with di- and triferrocenyl derivatives among them.

Original languageEnglish
Article number1490
Pages (from-to)1455-1463
Number of pages9
JournalMonatshefte fur Chemie
Volume146
Issue number9
DOIs
Publication statusPublished - Sep 7 2015

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Keywords

  • Copper
  • Cycloadditions
  • Homogeneous catalysis
  • Iodotriazole
  • Metallocenes
  • Palladium

ASJC Scopus subject areas

  • Chemistry(all)

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