74610-75-6Relevant academic research and scientific papers
Rate enhancing ligands for lead(IV)-mediated arylations
Buston, Jonathan E.H.,Moloney, Mark G.,Parry, Abigail V.L.,Wood, Paul
, p. 3407 - 3409 (2002)
The level of acceleration of the reactions of aryllead(IV) tricarboxylates with β-dicarbonyl reagents in the presence of several catalysts has been determined; in the case of 1,10-phenanthroline, almost a thousandfold increase in rate over the uncatalysed
Organocatalytic Enantioselective Decarboxylative Protonation Reaction of Meldrum's Acid Derivatives under PTC Conditions
Legros, Fabien,Martzel, Thomas,Brière, Jean-Fran?ois,Oudeyer, Sylvain,Levacher, Vincent
supporting information, p. 1975 - 1983 (2018/05/15)
An original organocatalyzed enantioselective protonation sequence of a transient quaternary ammonium enolate species has been developed by starting from readily available disubstituted Meldrum's acid derivatives and phenols. Under phase-transfer-catalytic (PTC) conditions, chiral nonracemic 2-aryl propionic ester derivatives were obtained in good isolated yields with enantioselectivities up to 70 % ee. The usefulness of the approach was demonstrated by the synthesis of enantioenriched (S)-ibuprofen.
The Chemistry of Aryllead(IV) Tricarboxylates. Reaction with Derivatives of Malonic Acid: New Routes to α-Aryl Carboxylic Acids and Arylated Barbituric Acid Derivatives
Kopinski, Richard P.,Pinhey, John T.,Rowe, Bruce A.
, p. 1245 - 1254 (2007/10/02)
Derivatives of 2,2-dimethyl-1,3-dioxan-4,6-dione (Meldrum's acid) and the sodium salts of substituted malonic esters undergo electrophilic C-arylation in high yield with aryllead triacetates, thus providing new routes to α-arylalkanoic acids.Syntheses of the antiflammatory compound 2-(p-isobutylphenyl)propanoic acid (Ibuprofen) have been carried out to demonstrate the method.The arylation reaction has been extended to 5-ethylbarbituric acid and to barbituric acid itself, which affords the 5,5-diarylated derivatives in good yield.A study of the effect of some tertiary bases on the reaction of p-methoxyphenyllead triacetate with the 5-isopropyl derivative of Meldrum's acid has shown that replacement of pyridine by 2,2'-bipyridyl results in an increase in yield and reaction rate, while a further marked improvement occurs in the presence of 1,10-phenanthroline.
THE α-ARYLATION OF DERIVATIVES OF MALONIC ACID WITH ARYLLEAD TRIACETATES. NEW SYNTHESES OF IBUPROFEN AND PHENOBARBITAL.
Pinhey, John T.,Rowe, Bruce A.
, p. 965 - 968 (2007/10/02)
Derivatives of Meldrum's acid and the sodium salts of substituted malonic acid esters undergo rapid arylation in high yield when treated with aryllead triacetates.These reactions have been applied to the synthesis of ibuprofen, an analgesic, and in a closely related reaction 5-ethylbarbituric acid has been reacted with phenyllead triacetate to give phenobarbital.
