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Bis-alkoxycarbonylation of styrene by pyridinimine palladium catalysts (Articolo in rivista)
- Type
- Label
- Bis-alkoxycarbonylation of styrene by pyridinimine palladium catalysts (Articolo in rivista) (literal)
- Anno
- 2002-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1039/b108804c (literal)
- Alternative label
Bianchini, Claudio; Lee, Hon Man; Mantovani, Giuseppe; Meli, Andrea; Oberhauser, Werner (2002)
Bis-alkoxycarbonylation of styrene by pyridinimine palladium catalysts
in New journal of chemistry (1987)
(literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Bianchini, Claudio; Lee, Hon Man; Mantovani, Giuseppe; Meli, Andrea; Oberhauser, Werner (literal)
- Pagina inizio
- Pagina fine
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
- Rivista
- Note
- ISI Web of Science (WOS) (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
- Titolo
- Bis-alkoxycarbonylation of styrene by pyridinimine palladium catalysts (literal)
- Abstract
- Pyridinimine-modified Pd(II) complexes of general formulae (N-N0)Pd(Y)2 catalyze the methoxycarbonylation
of styrene to give dimethyl phenylsuccinate as the largely major product [N-N0 ¼py-2-C(R)=N(2,6-R0C6H3),
R¼H, Me; R0 ¼Me, i-Pr; 6-Mepy-2-C(H)=N[2,6-(i-Pr)2C6H3]; py-2-C(H)=N(C6H5); Y¼acetate,
trifluoroacetate]. The influence of various catalytic parameters on the overall conversion of styrene to
carbonylated products and on the product selectivity has been studied by systematically varying the type of
palladium initiator, the concentrations of organic oxidant (1,4-benzoquinone) and protic acid
(p-toluenesulfonic acid), and the CO pressure. By an appropriate choice of the structure of the pyridinimine
ligand and of the reaction parameters, turn-over numbers as high as 96 and selectivities in dimethyl
phenylsuccinate as high as 98% were obtained. In particular, the overall conversion of styrene is controlled by
the steric properties of the alkyl substituents on the imine aryl group, while the nature of the substituent
(H or Me) on the imine carbon influences the selectivity. The addition of 2 equivalents of TsOH to the catalytic
mixtures generally increased the styrene conversion but lowered the selectivity in dimethyl phenylsuccinate due
to greater production of methyl 3,6-diphenyl-4-oxohexanoate. Further additions of TsOH (up to 6 equivalents)
resulted in better selectivities and lower conversions for all precursors. (literal)
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