An efficient [2+3] cycloaddition approach to the synthesis of pyridyl-appended fullerene ligands

Pavel A. Troshin, Alexander S. Peregudov, David Mühlbacher, Rimma N. Lyubovskaya

Research output: Contribution to journalArticlepeer-review

62 Citations (Scopus)

Abstract

We have used 2-, 3-, and 4-picolylamines and their various N-substituted derivatives as substrates to generate azomethine ylides for [2+3] cycloaddition to [60]fullerene. A considerable difference in the reactivity of isomeric picolylamines was observed; however, even less reactive 3-picolylamines afford high yields of products under acid or base catalysis. This method provides easy access to a large family of valuable ligands (pyridyl-substituted pyrrolidinofullerenes) that can be used in the design of transition-metal complexes and non-covalently bonded dyads with metalloporphyrins. Unusually high yields of products and convenience of synthetic procedures (2-10 min heating the reagents at reflux in 1,2-dichlorobenzene in air in most cases) as well as a wide synthetic potential make this reaction a good alternative to the commonly used Prato method.

Original languageEnglish
Pages (from-to)3064-3074
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number14
DOIs
Publication statusPublished - 11 Jul 2005
Externally publishedYes

Keywords

  • Azomethine ylides
  • Cycloaddition
  • Fullerenes
  • N ligands
  • Picolylamines

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