Development of catalytic reactions using n-sulfonyl-1,2,3-triazoles as precursors of carbene complexes

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10 Citations (Scopus)

Abstract

N-Sulfonyl-1,2,3-triazoles are readily prepared by a copper (I)-catalyzed 1,3-dipolar cycloaddition reaction of terminal alkynes with sulfonyl azides. Their ring-chain tautomerization generates α - imino diazo compounds, although the equilibrium lies far to the triazole form in general. Transition metal catalysts, especially rhodium(II) carboxylate dimers, can efficiently trap the transient α-imino diazo compounds to give α-imino metal carbene complexes with the extrusion of molecular nitrogen. These metal carbene complexes share many features with the well-known α-oxo metal carbene complexes derived from α-dizao carbonyl compounds. However, in some cases, the presence of the nucleophilic imino nitrogen endows their unique reactivity depending on the reactants as well as the catalysts. In this article, we describe nickel (0) and rhodium (II)-catalyzed inter- and intramolecular reactions of N-sulfonyl-1,2,3-triazoles with various types of reactants such as carbon, oxygen, and sulfur nucleophiles, which provide a facile method for the synthesis of nitrogen-containing compounds. These reactions are successfully applied to all- in one-pot reactions starting from terminal alkynes.

Original languageEnglish
Pages (from-to)1200-1211
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume73
Issue number12
DOIs
Publication statusPublished - 2015
Externally publishedYes

Keywords

  • Carbene complexes
  • Nickel
  • Nitrogen-containing compounds
  • One -pot reaction
  • Rhodium
  • Triazoles

ASJC Scopus subject areas

  • Organic Chemistry

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