Pd/Al2O3-catalysed redox isomerisation of allyl alcohol: Application in aldol condensation and oxidative heterocyclization reactions

Dániel Zsolnai, Péter Mayer, K. Szöri, Gábor London

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The application of the Pd/Al2O3 catalyst in allyl alcohol isomerization and subsequent aldol condensation and heterocyclization reactions is described. The activity of Pd/Al2O3 in these transformations is suggested to be due to the participation of the Lewis acidic sites of the support in the activation of the alcohol towards oxidative dehydrogenation by the metal and subsequent hydride transfer. The resulting enol(ate)/aldehyde could undergo further reactions promoted by the acid-base properties of the support. In the aldol condensation reactions of the isomerization product, electron poor aromatic aldehydes and heteroaromatic aldehydes showed the highest activity, while aromatic aldehydes bearing electron donating substituents reacted after transformation to the corresponding N-tosyl imines. 1,2-Disubstituted aromatics gave heterocyclic products in one-pot multistep reaction sequences.

Original languageEnglish
Pages (from-to)3814-3820
Number of pages7
JournalCatalysis Science and Technology
Volume6
Issue number11
DOIs
Publication statusPublished - 2016

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Isomerization
Aldehydes
Condensation
Alcohols
Bearings (structural)
Imines
Condensation reactions
Electrons
Dehydrogenation
Hydrides
Metals
Chemical activation
Catalysts
Acids
Oxidation-Reduction
3-hydroxybutanal
allyl alcohol

ASJC Scopus subject areas

  • Catalysis

Cite this

Pd/Al2O3-catalysed redox isomerisation of allyl alcohol : Application in aldol condensation and oxidative heterocyclization reactions. / Zsolnai, Dániel; Mayer, Péter; Szöri, K.; London, Gábor.

In: Catalysis Science and Technology, Vol. 6, No. 11, 2016, p. 3814-3820.

Research output: Contribution to journalArticle

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