The aminocarbonylation of phenylacetylene has been studied in the presence of the catalytic system formed by palladium acetate in combination with (2-pyridyl)diphenylphosphine and methanesulfonic acid. The catalytic activity is strongly influenced by the nature of the amine: good reaction rates are achieved using amines of low basicity such as aniline. The reaction solvent influences both the activity and the selectivity of the catalyst: the highest reaction rates accompanied by complete regioselectivity towards the branched amide are obtained working in dichloromethane/N-methylpyrrolidinone mixtures. Also the acid to palladium molar ratio and the P(CO) affect to a lower extent the process: the highest catalyst activity is obtained operating at a methanesulfonic acid/Pd molar ratio of 30:1 and at P(CO) = 20 atm.

Aminocarbonylation of phenylacetylene catalysed by palladium acetate in combination with (2-pyridyl)diphenylphosphine and methanesulfonic acid

MATTEOLI, Ugo;SCRIVANTI, Alberto;BEGHETTO, Valentina
2004

Abstract

The aminocarbonylation of phenylacetylene has been studied in the presence of the catalytic system formed by palladium acetate in combination with (2-pyridyl)diphenylphosphine and methanesulfonic acid. The catalytic activity is strongly influenced by the nature of the amine: good reaction rates are achieved using amines of low basicity such as aniline. The reaction solvent influences both the activity and the selectivity of the catalyst: the highest reaction rates accompanied by complete regioselectivity towards the branched amide are obtained working in dichloromethane/N-methylpyrrolidinone mixtures. Also the acid to palladium molar ratio and the P(CO) affect to a lower extent the process: the highest catalyst activity is obtained operating at a methanesulfonic acid/Pd molar ratio of 30:1 and at P(CO) = 20 atm.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10278/27749
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