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Keywords:

  • domino reactions;
  • heterogenized catalysts;
  • metal organic frameworks;
  • one-pot reaction;
  • postfunctionalization

Abstract

We describe the postsynthetic modification of Zr-based metal organic frameworks (MOFs) containing chiral NNN-pincer ligands based on aminopyridineimines, as well as the subsequent formation of (NNN)-M-Zr-MOF complexes (M=Rh, Ir). With these new multifunctional materials, we performed a cascade of condensation reactions followed by hydrogenation of the resulting double bond. If the condensation reaction occurs between an aldehyde and ethyl nitroacetate, (NNN)–M–Zr-MOF complexes catalyze the one-pot synthesis of nitroalkenes, in which ZrIV Lewis sites play a role similar to that of the generally used TiIV in homogeneous catalysis. These multifunctional hybrid catalysts retain their crystalline framework even after the reaction, and they were isolated easily from the reaction mixture through filtration and reused several times without a significant degradation in activity. Moreover, there was no contribution from leached active species and conversion was possible only in the presence of the solid catalyst.