TY - JOUR
T1 - Palladium complexes grafted onto mesoporous silica catalysed the double carbonylation of aryl iodides with amines to give α-ketoamides
AU - Genelot, Marie
AU - Villandier, Nicolas
AU - Bendjeriou, Anissa
AU - Jaithong, Patchareeporn
AU - Djakovitch, Laurent
AU - Dufaud, Véronique
PY - 2012/9
Y1 - 2012/9
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84864668296&partnerID=8YFLogxK
U2 - 10.1039/c2cy00516f
DO - 10.1039/c2cy00516f
M3 - Article
AN - SCOPUS:84864668296
SN - 2044-4753
VL - 2
SP - 1886
EP - 1893
JO - Catalysis Science and Technology
JF - Catalysis Science and Technology
IS - 9
ER -