Search results for "Baylis–Hillman reaction"

showing 3 items of 3 documents

Polystyrene-supported proline as recyclable catalyst in the Baylis–Hillman reaction of arylaldehydes and methyl or ethyl vinyl ketone

2008

Abstract Polystyrene-supported proline has been used as co-organocatalyst (10 mol%) with imidazole (10 mol%) in the Baylis–Hillman reaction between methyl or ethyl vinyl ketone and arylaldehydes. Recycling studies showed that the proline resin can be used up to five cycles with high isolated yields. This study represents the first example of supported proline as heterogeneous catalyst in the above reaction and broaden the scope of this catalytic material.

chemistry.chemical_classificationKetoneProcess Chemistry and TechnologySettore CHIM/06 - Chimica OrganicaGeneral ChemistryHeterogeneous catalysisorganocatalysis heterogeneous catalysis Baylis-Hilmann reactionCatalysisCatalysischemistry.chemical_compoundchemistryOrganocatalysisImidazoleOrganic chemistryBaylis–Hillman reactionPolystyreneProlineCatalysis Communications
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First Evidence of Proline Acting as a Bifunctional Catalyst in the Baylis–Hillman Reaction Between Alkyl Vinyl Ketones and Aryl Aldehydes

2008

Proline in the presence of sodium hydrogen carbonate has been found to be an effective catalyst for the Baylis–Hillman reaction between methyl or ethyl vinyl ketone and aryl aldehydes. Screening of several amine catalysts showed that an ionizable carboxylic function directly linked to the secondary amine catalyst plays an important role in the synthesis of the desired product in good yield. The data obtained has allowed us to suggest, for the first time, that proline, sarcosine, pipecolinic acid and homoproline may act as bifunctional catalysts via a bicyclic enaminolactone species as intermediate. Quantum-mechanical calculations (PM3/COSMO and ab initio 3-21G/COSMO) support this mechanism …

chemistry.chemical_classificationKetoneProlineAldehydeArylOrganic ChemistrySemi-empiricalcalculationSettore CHIM/06 - Chimica OrganicaBifunctional catalystCatalysisOrganocatalysichemistry.chemical_compoundchemistryOrganocatalysisOrganic chemistryAmine gas treatingBaylis–Hillman reactionPhysical and Theoretical ChemistryBaylis–Hillman reactionBifunctionalReaction mechanismEuropean Journal of Organic Chemistry
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ChemInform Abstract: First Evidence of Proline Acting as a Bifunctional Catalyst in the Baylis-Hillman Reaction Between Alkyl Vinyl Ketones and Aryl …

2008

Proline in the presence of sodium hydrogen carbonate has been found to be an effective catalyst for the Baylis–Hillman reaction between methyl or ethyl vinyl ketone and aryl aldehydes. Screening of several amine catalysts showed that an ionizable carboxylic function directly linked to the secondary amine catalyst plays an important role in the synthesis of the desired product in good yield. The data obtained has allowed us to suggest, for the first time, that proline, sarcosine, pipecolinic acid and homoproline may act as bifunctional catalysts via a bicyclic enaminolactone species as intermediate. Quantum-mechanical calculations (PM3/COSMO and ab initio 3-21G/COSMO) support this mechanism …

chemistry.chemical_classificationchemistry.chemical_compoundKetonechemistryBicyclic moleculeArylOrganic chemistryAmine gas treatingBaylis–Hillman reactionGeneral MedicineBifunctionalBifunctional catalystCatalysisChemInform
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