Poster (Scientific congresses and symposiums)
Synthesis of new palladium complexes containing a sulfonamide ligand and their catalytic evaluation in carbene chemistry
Etse, Koffi Senam; Hans, Morgan; Delaude, Lionel et al.
2013Journée du Département de Chimie
 

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Keywords :
sulfonamides, crystals structures; palladium complexes; cyclopropanation
Abstract :
[en] Since their first synthesis, sulfonamides and their derivatives have attracted the interest of many biochemists’ due to their importance in medicinal chemistry. Afterward, the development of organometallic chemistry gave new interest to sulfonamide compounds. Metal complexes containing sulfonamides ligands represent interesting organometallics molecules due to their different catalytic proprieties. Here we present the first result of the optimised way to prepare palladium complexes containing sulfonamides ligands, their crystals structures and catalytic activity in cyclopropanation reaction of styrene.The new complexes were prepared quantitatively by reacting Pd(PPh3)4 and 2-halogenobenzenesulfonamides. In the case of the iodide, the reaction proceeded at room temperature for 4 hours. The precipitate is filtered after 4 h on a Buchner funnel, washed with toluene and pentane. For the complexes containing bromides, the reaction was carried out at 70 °C for 12 hours. All these complexes were characterized by various NMR methods. . In 31P NMR, all the complexes show two doublets and one singlet. The analysis reveals that the singlet can be assigned easily to the trans isomer and the two speared doublet for the cis one. The trans isomer is obtain as a major product. the high steric hindrance of the mesithyl (Mes) group leads to more formation of the cis isomer. The catalytic activity of the four complexes are evaluated in cyclopropanation reaction of styrene with EtDA (of ethyl diazoacetate). To enhance selectivity for the cyclopropane, EtDA was added slowly via a pump syringe to a solution of styrene and catalyst. The yields are determined by GC based on EtDA. Results show that independently of the mixture of cis and trans isomers, ester cyclopropane is obtained in good yield. In all instances, the trans cyclopropane was the major product.In conclusion, we have shown an easy way to prepare novel palladium complexes bearing sulfonamide ligand. The sulfonamide substituent in ortho position of the phenyl linked to the palladium leads to the formation of the cis and trans complexes isomer. The structures of the trans complexes were confirmed by X-ray crystallographic analysis. The catalytic activity of all the complexes in cyclopropanation of styrene leads to good yield with selectivity for the trans cyclopropane.
Research center :
Chimie macromoléculaire et catalyse organique
Disciplines :
Chemistry
Author, co-author :
Etse, Koffi Senam ;  Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Hans, Morgan;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Delaude, Lionel  ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène
Demonceau, Albert ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Language :
English
Title :
Synthesis of new palladium complexes containing a sulfonamide ligand and their catalytic evaluation in carbene chemistry
Publication date :
05 September 2013
Number of pages :
A0
Event name :
Journée du Département de Chimie
Event organizer :
ULg - Université de Liège
Event place :
Liège, Belgium
Event date :
05 septembre 2013
Available on ORBi :
since 21 January 2020

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