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Synthesis of novel room temperature chiral ionic liquids. application as reaction media for the heck arylation of aza-endocyclic acrylates

Pastre, Julio C. and Génisson, Yves and Saffon, Nathalie and Dandurand, Jany and Correia, Carlos R. D. Synthesis of novel room temperature chiral ionic liquids. application as reaction media for the heck arylation of aza-endocyclic acrylates. (2010) Journal of the Brazilian Chemical Society, vol. 21 (n° 5). ISSN 0103-5053

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Official URL: http://dx.doi.org/10.1590/S0103-50532010000500009

Abstract

New achiral and chiral RTILs were prepared using novel and/or optimized synthetic routes. These new series of imidazolinium, imidazolium, pyridinium and nicotine-derived ionic liquids were fully characterized including differential scanning calorimetry (DSC) analysis. The performance of these achiral and chiral room temperature ionic liquids (RTILs) was demonstrated by means of the Heck arylation of endocyclic acrylates employing arenediazonium salts and aryl iodides. The Heck arylations performed in the presence of these ionic entities, either as a solvent or as an additive, were effective leading to complete conversion of the substrate and good to excellent yield of the Heck adduct. In spite of the good performances, no asymmetric induction was observed in any of the cases studied. Two new diastereoisomeric NHC-palladium complexes were prepared in good yields from a chiral imidazolium salt and their structure characterized by X-ray diffraction. Overall, the Heck arylations employing arenediazonium tetrafluoroborates in RTILs were more effective than the traditional protocols employing aryl iodides in terms of reactivity and yields.

Item Type:Article
Additional Information:Thanks to Sociedade Brasileira de Quimica editor. The definitive version is available at http://www.sbq.org.br/ The original PDF of the article can be found at Journal of the Brazilian Chemical Society website : http://jbcs.sbq.org.br/
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS
Université de Toulouse > Institut National Polytechnique de Toulouse - INPT
French research institutions > Institut de Recherche pour le Développement - IRD
Other partners > Universidade Estadual de Campinas - Unicamp (BRAZIL)
Université de Toulouse > Université Paul Sabatier-Toulouse III - UPS
Laboratory name:
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Deposited By:Leila Abdelouhab

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