Experimental and Theoretical Approaches to the Influence of the Addition of Pyrene to a Series of Pd and Ni NHC-Based Complexes: Catalytic Consequences
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Otros documentos de la autoría: Valdés Rivas, Hugo Christian; Poyatos, Macarena; Ujaque, Gregori; Peris, Eduardo
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Título
Experimental and Theoretical Approaches to the Influence of the Addition of Pyrene to a Series of Pd and Ni NHC-Based Complexes: Catalytic ConsequencesFecha de publicación
2014-11-20Editor
WileyISSN
0947-6539; 1521-3765Cita bibliográfica
VALDÉS, Hugo, et al. Experimental and Theoretical Approaches to the Influence of the Addition of Pyrene to a Series of Pd and Ni NHC‐Based Complexes: Catalytic Consequences. Chemistry-A European Journal, 2015, vol. 21, no 4, p. 1578-1588.Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
http://onlinelibrary.wiley.com/doi/10.1002/chem.201404618/fullPalabras clave / Materias
Resumen
A series of Ni and Pd complexes with three different N-heterocyclic carbene (NHC)-based ligands (imidazolylidene, benzimidazolylidene and pyrene–imidazolylidene) has been prepared and fully characterized. The influence ... [+]
A series of Ni and Pd complexes with three different N-heterocyclic carbene (NHC)-based ligands (imidazolylidene, benzimidazolylidene and pyrene–imidazolylidene) has been prepared and fully characterized. The influence of the addition of pyrene to solutions containing these complexes is studied by means of NMR and UV/Vis spectroscopies and by cyclic voltammetry. The addition of pyrene to the pyrene–NHC-containing Pd and Ni complexes gives rise to the formation of adducts by π–π stacking interactions between pyrene and the pyrene group of the NHC ligand. This interaction causes a modification of the electronic properties of the metal, as demonstrated by cyclic voltammetric studies of the Ni–NHC complexes. Theoretical calculations support this type of π-interactions, and justify the higher interactions observed with the pyrene–NHC containing complexes. The catalytic activities of the complexes were tested in the Suzuki–Miyaura C[BOND]C coupling and in the α-arylation of ketones. The addition of pyrene as an external π-stacking additive does not affect the activities of the complexes in the Suzuki–Miyaura coupling, but this observation may be justified due to the fact that the process is heterogeneously catalyzed, as indicated by the mercury-drop test. The addition of pyrene to the catalytic α-arylation of ketones results in a decrease in the activity of the reactions catalyzed by the pyrene–imidazolylidene palladium complex, whereas the other two catalysts do not modify their activity in the presence of this π-stacking additive. [-]
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Chemistry-A European Journal, 21, (2015)Derechos de acceso
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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