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

Yugang Cui; Ilaria Biondi; Manish Chaubey; Xue Yang; Zhaofu Fei; Rosario Scopelliti; Christian G. Hartinger; Yongdan Li; Cinzia Chiappe; Paul J. Dyson

doi:10.1039/B920025H

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

Yugang Cui,^ab Ilaria Biondi,^a Manish Chaubey,^a Xue Yang,^ab Zhaofu Fei,^a Rosario Scopelliti,^a Christian G. Hartinger,^a Yongdan Li,^b Cinzia Chiappe^c and Paul J. Dyson*^a

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* Corresponding authors

^a Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland
E-mail: paul.dyson@epfl.ch

^b Department of Catalysis Science and Technology, School of Chemical Engineering, Tianjin University, Tianjin, P. R. China

^c Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, 56126 Pisa, Italy

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.

This article is part of the themed collection: Ionic Liquids

Physical Chemistry Chemical Physics

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

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

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