Five imidazolium-based materials have been synthesised and used for the first time as palladium scavengers. Radical reactions of suitable bis-vinylimidazolium salts led to a series of insoluble materials through homo-polymerisation, immobilisation with a 3-mercaptopropyl-modified silica gel or co-polymerisation with ethylene glycol dimethylacrylate. These materials were screened as palladium scavengers with a set of palladium(0) and palladium(II) compounds in different solvents and at different starting amounts of palladium. In many cases, residual amounts of palladium were lower than 5 ppm, as requested for the manufacture of active pharmaceutical ingredients and fine chemicals. The application of one of these materials as a palladium scavenger in a Suzuki coupling reaction resulted in a 29-fold abatement of the palladium content in the final product with respect to the control reaction.

Buscemi, R., Giacalone, F., Orecchio, S., Gruttadauria, M. (2014). Cross-Linked Imidazolium Salts as Scavengers for Palladium. CHEMPLUSCHEM, 79(3), 421-426 [10.1002/cplu.201300361].

Cross-Linked Imidazolium Salts as Scavengers for Palladium

BUSCEMI, Roberto;GIACALONE, Francesco;ORECCHIO, Santino;GRUTTADAURIA, Michelangelo
2014-01-01

Abstract

Five imidazolium-based materials have been synthesised and used for the first time as palladium scavengers. Radical reactions of suitable bis-vinylimidazolium salts led to a series of insoluble materials through homo-polymerisation, immobilisation with a 3-mercaptopropyl-modified silica gel or co-polymerisation with ethylene glycol dimethylacrylate. These materials were screened as palladium scavengers with a set of palladium(0) and palladium(II) compounds in different solvents and at different starting amounts of palladium. In many cases, residual amounts of palladium were lower than 5 ppm, as requested for the manufacture of active pharmaceutical ingredients and fine chemicals. The application of one of these materials as a palladium scavenger in a Suzuki coupling reaction resulted in a 29-fold abatement of the palladium content in the final product with respect to the control reaction.
2014
Buscemi, R., Giacalone, F., Orecchio, S., Gruttadauria, M. (2014). Cross-Linked Imidazolium Salts as Scavengers for Palladium. CHEMPLUSCHEM, 79(3), 421-426 [10.1002/cplu.201300361].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/90165
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