Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds

Sergei F. Vasilevsky, Olga L. Krivenko, Igor V. Alabugin

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI-PPh3-K2CO3-DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the formation of 4-[2-(aryl/hetarylethynyl)phenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyls in 70-75% yields.

Original languageEnglish
Pages (from-to)8246-8249
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number46
DOIs
Publication statusPublished - 12 Nov 2007
Externally publishedYes

Keywords

  • 3-Imidazoline-nitroxyles
  • Aryl- and hetarylacetylenes
  • Cross-coupling
  • Oxidative coupling
  • Stable radicals

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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