Synthetic and mechanistic aspects of cross-coupling of nitroxyl radicals of 3-imidazoline series with terminal alkynes

Sergei F. Vasilevsky, Olga L. Krivenko, Vitalii R. Gorelik, Igor V. Alabugin

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Practical synthetic approaches to the new class of acetylenic derivatives of 3-imidazolyl-3-oxide-1-oxyls, including biradicals, were developed through cross-coupling reactions of 3-imidazolyl halides with either terminal alkynes or their copper salts. The presence of nitroxyl functional group as an internal oxidant leads to a competition between the formation of cross-coupling products and the products of oxidative homocoupling. The balance in this competition can be shifted toward the cross-coupling products through the combination of factors that includes nature of the catalyst, reactivity of the halides, and reaction conditions.

Original languageEnglish
Pages (from-to)8807-8814
Number of pages8
JournalTetrahedron
Volume64
Issue number37
DOIs
Publication statusPublished - 8 Sep 2008
Externally publishedYes

Keywords

  • 3-Imidazolyl-3-oxide-1-oxyls
  • Copper salts of alkynes
  • Cross-coupling
  • Homocoupling
  • Nitronylnitroxyl radicals (NNR)
  • Terminal alkynes
  • Transition metal catalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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