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Issue 8, 2010
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Nitrile-functionalized pyrrolidinium ionic liquids as solvents for cross-coupling reactions involving in situ generated nanoparticlecatalyst reservoirs

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Abstract

A series of nitrile-functionalized pyrrolidinium-based ionic liquids have been prepared and characterized by spectroscopic methods and X-ray crystallography. The application of these new ionic liquids as reaction media for Suzuki and Stille C–C cross-coupling reactions has been investigated and compared with related imidazolium and pyridinium systems (including those with and without nitrile functionalities). The nature of the ionic liquid strongly influences the catalyzed reaction and it would appear that, in addition to the nitrile group, the strength of anion–cation pairing in the ionic liquid and the viscosity of the ionic liquid play critical roles. Nanoparticles are also detected following catalysis and their role, and the influence of the ionic liquid on them, is assessed. The ability to use the nitrile-functionalized pyrrolidinium-based ionic liquids diluted in other (non-functionalized) ionic liquids is also described.

Graphical abstract: Nitrile-functionalized pyrrolidinium ionic liquids as solvents for cross-coupling reactions involving in situ generated nanoparticle catalyst reservoirs

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Article information


Submitted
25 Sep 2009
Accepted
19 Nov 2009
First published
21 Dec 2009

Phys. Chem. Chem. Phys., 2010,12, 1834-1841
Article type
Paper

Nitrile-functionalized pyrrolidinium ionic liquids as solvents for cross-coupling reactions involving in situ generated nanoparticle catalyst reservoirs

Y. Cui, I. Biondi, M. Chaubey, X. Yang, Z. Fei, R. Scopelliti, C. G. Hartinger, Y. Li, C. Chiappe and P. J. Dyson, Phys. Chem. Chem. Phys., 2010, 12, 1834
DOI: 10.1039/B920025H

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