Immobilized DMAP derivatives rivaling homogeneous DMAP

Valerio D Elia, Yinghao Liu, Hendrik Zipse*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

The copper-catalyzed Huisgen reaction between azides and alkynes was utilized to covalently attach derivatives of 4-(dimethylamino)pyridine (DMAP) to a polystyrene resin (PS) support. The catalytic potential of these constructs as determined in acylation and aza-Morita-Baylis-Hillman reactions far exceeds that of commercially available DMAP-PS resins and is fully competitive with DMAP in homogeneous solution. Immobilization of 3,4-diaminopyridine catalysts on polystyrene by using the copper-catalyzed Huisgen reaction allowed the preparation of new supported catalysts ofunprecedented catalytic activity in acylation and aza-Morita-Baylis-Hillman reactions.

Original languageEnglish (US)
Pages (from-to)1527-1533
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
StatePublished - Mar 1 2011

Keywords

  • Acylation
  • Homogeneous catalysis
  • Immobilization
  • Organocatalysis
  • Supported catalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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