111223-41-7Relevant academic research and scientific papers
SYNTHESE DE DIENES-1,3 ET DE STYRENES FONCTIONNALISES PAR CARBOPALLADATION CATALYTIQUE D'ALLENES
Ahmar, Mohammed,Cazes, Bernard,Gore, Jacques
, p. 4505 - 4508 (1984)
The palladium (0) catalysed reaction of aryl and vinyl halides in the presence of sodium ethyl malonate leads with good yields and in certain cases with high stereoselectivity to styrenes and 1,3-butadienes derivatives.
CARBOPALLADATION OF ALLENIC HYDROCARBONS. A NEW WAY TO FUNCTIONALIZED STYRENES AND 1,3-BUTADIENES.
Ahmar, Mohammed,Barieux, Jean-Jacques,Cazes, Bernard,Gore, Jacques
, p. 513 - 526 (2007/10/02)
The palladium-catalyzed coupling reaction of allenes, vinyl or aryl halides and stabilized carbanions is described: ?-allyl palladium complexes are formed by addition of a vinyl or an aryl-palladium complex to an allenic hydrocarbon and trapped by the sodium enolate of diethyl malonate giving rise with good yields to β-butadienyl or β-styryl malonates.With monoalkyl allenes, the reaction is regiospecific with attack of the nucleophile on the unsubstituted carbon of the intermediate ?-allyl complex and in many cases highly stereoselective with the predominant formation of the E configuration for the trisubstituted double bond of the diene.This configuration was demonstrated by 1H NMR using NOE difference spectroscopy.
