Palladium complexes grafted onto mesoporous silica catalysed the double carbonylation of aryl iodides with amines to give α-ketoamides

Marie Genelot, Nicolas Villandier, Anissa Bendjeriou, Patchareeporn Jaithong, Laurent Djakovitch*, Véronique Dufaud

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

A promising route for the double carbonylation of aryl iodide derivatives with secondary and primary amines to produce α-ketoamides is described using covalently immobilized palladium complexes on SBA-15 silica. Adequate adjustments of the different reaction parameters (temperature, CO pressure, nature of base, solvent, substrate...) to achieve optimal catalyst performance were made using PdCl 2(PPh 2) 2@SBA-15 as catalytic system. High conversions (up to 80%) and excellent selectivities (up to 96%) for the double carbonylated α-ketoamide products were obtained using K 2CO 3 as base, MEK or DMF as solvent and a 1 mol% [Pd] catalyst. We also demonstrated that two other palladium hybrid mesoporous materials can be alternatively used, namely PdCl 2(PCy 2) 2@SBA-15 and PdCl 2(PNP)@SBA-15, without loss of activity and selectivity. Finally, catalyst recycling of PdCl 2(PPh 2) 2@SBA-15 showed that the catalyst could be reused for up to 3 cycles without affecting catalyst performance.

Original languageEnglish (US)
Pages (from-to)1886-1893
Number of pages8
JournalCatalysis Science and Technology
Volume2
Issue number9
DOIs
StatePublished - Sep 2012
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis

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