Tandem Catalysis of an Aldol-'Click' Reaction System within a Molecular Hydrogel

Molecules. 2016 Jun 8;21(6):744. doi: 10.3390/molecules21060744.

Abstract

A heterogeneous supramolecular catalytic system for multicomponent aldol-'click' reactions is reported. The copper(I) metallohydrogel functionalized with a phenyltriazole fragment was able to catalyze the multicomponent reaction between phenylacetylene, p-nitrobenzaldehyde, and an azide containing a ketone moiety, obtaining the corresponding aldol products in good yields. A possible mechanistic pathway responsible for this unexpected catalytic behavior has been proposed.

Keywords: aldol addition; click reaction; multicomponent system; supramolecular gels; tandem catalysis.

MeSH terms

  • Acetylene / analogs & derivatives
  • Acetylene / chemistry
  • Aldehydes / chemistry
  • Azides / chemistry
  • Benzaldehydes / chemistry
  • Catalysis
  • Click Chemistry*
  • Copper / chemistry
  • Hydrogel, Polyethylene Glycol Dimethacrylate / chemistry*
  • Ketones / chemistry*
  • Metals / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Azides
  • Benzaldehydes
  • Ketones
  • Metals
  • phenylacetylene
  • Hydrogel, Polyethylene Glycol Dimethacrylate
  • Copper
  • 3-hydroxybutanal
  • Acetylene
  • benzaldehyde