A new step towards solid base catalysis: Azidoproazaphosphatranes immobilized in nanopores of mesoporous silica

Pascal Dimitrov Raytchev, Anissa Bendjeriou-Sedjerari, Jean Pierre Dutasta*, Alexandre Martinez, Véronique Dufaud

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Heterogeneous basic catalysts derived from proazaphosphatranes, known as Verkade's superbases, were prepared for the first time by covalent immobilization onto SBA-15 silica. In order to introduce the tether to the surface, three siloxane-containing azido derivatives of the proazaphosphatranes were first synthesized (2a-c) which after post-synthetic grafting onto silica support led to the formation of hybrid materials of different basicity and steric properties, 2a-c@SBA-15. These latter were fully characterized using a wide variety of molecular and solid-state techniques to determine their structural and textural properties. These new solid base catalysts were then evaluated in the Diels-Alder reactions of anthrone and 3-hydroxy-2-pyrone with two electron-deficient dienophiles, N-methylmaleimide and dimethyl fumarate. In general, high activity and selectivity were obtained depending on the catalytic species, the performance decreasing in the order methoxybenzyl>neopentyl> methyl azidophosphatrane. Catalyst recycling was studied for the best catalyst, the methoxybenzyl derivative, 2c@SBA-15, and it was shown that the catalyst could be re-used up to 3 cycles before any loss of activity could be detected.

Original languageEnglish (US)
Pages (from-to)2067-2077
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number11-12
DOIs
StatePublished - Aug 1 2011

Keywords

  • Diels-Alder reaction
  • hybrid materials
  • mesoporous silica
  • non-ionic bases
  • organocatalysis
  • proazaphosphatranes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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