Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts

Cinzia Pavia, Francesco Giacalone, Lucia Anna Bivona, Anna Maria Pia Salvo, Chiara Petrucci, Giacomo Strappaveccia, Luigi Vaccaro, Carmela Aprile, Michelangelo Gruttadauria

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

Palladium (10 wt%) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol% in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt%) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.

langue originaleAnglais
Pages (de - à)57-62
Nombre de pages6
journalJournal of Molecular Catalysis A: Chemical
Volume387
Les DOIs
étatPublié - 1 janv. 2014

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Palladium
palladium
Salts
salts
Scavenging
Alkenes
Iodides
Olefins
Metals
scavenging
iodides
Catalysts
alkenes
catalysts
products
metals

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Pavia, Cinzia ; Giacalone, Francesco ; Bivona, Lucia Anna ; Salvo, Anna Maria Pia ; Petrucci, Chiara ; Strappaveccia, Giacomo ; Vaccaro, Luigi ; Aprile, Carmela ; Gruttadauria, Michelangelo. / Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts. Dans: Journal of Molecular Catalysis A: Chemical. 2014 ; Vol 387. p. 57-62.
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abstract = "Palladium (10 wt{\%}) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol{\%} in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt{\%}) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.",
keywords = "CC cross-coupling, Heck reaction, Heterogeneous catalysis, Ionic liquids, Suzuki reaction",
author = "Cinzia Pavia and Francesco Giacalone and Bivona, {Lucia Anna} and Salvo, {Anna Maria Pia} and Chiara Petrucci and Giacomo Strappaveccia and Luigi Vaccaro and Carmela Aprile and Michelangelo Gruttadauria",
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Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts. / Pavia, Cinzia; Giacalone, Francesco; Bivona, Lucia Anna; Salvo, Anna Maria Pia; Petrucci, Chiara; Strappaveccia, Giacomo; Vaccaro, Luigi; Aprile, Carmela; Gruttadauria, Michelangelo.

Dans: Journal of Molecular Catalysis A: Chemical, Vol 387, 01.01.2014, p. 57-62.

Résultats de recherche: Contribution à un journal/une revueArticle

TY - JOUR

T1 - Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts

AU - Pavia, Cinzia

AU - Giacalone, Francesco

AU - Bivona, Lucia Anna

AU - Salvo, Anna Maria Pia

AU - Petrucci, Chiara

AU - Strappaveccia, Giacomo

AU - Vaccaro, Luigi

AU - Aprile, Carmela

AU - Gruttadauria, Michelangelo

PY - 2014/1/1

Y1 - 2014/1/1

N2 - Palladium (10 wt%) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol% in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt%) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.

AB - Palladium (10 wt%) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol% in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt%) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.

KW - CC cross-coupling

KW - Heck reaction

KW - Heterogeneous catalysis

KW - Ionic liquids

KW - Suzuki reaction

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