Palladium(0)-catalyzed substitution of allylic substrates in an aqueous-organic medium. Influence of various parameters on the selectivity of the reaction

The regioselectivity of the reaction of ethyl acetoacetate on allylic carbonate in the presence of a catalyst prepared from Pd(OAc) 2 and P(C 6H 4- m-SO 3Na) 3 (or tppts) is not affected by the ratio Pd(OAc) 2/tppts, the nature of the nitrile, the relative amounts of water and nitrile or the tempera...

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Bibliographic Details
Published in:Journal of molecular catalysis. A, Chemical Chemical, 1997-02, Vol.116 (1), p.289-296
Main Authors: Sigismondi, Silvana, Sinou, Denis
Format: Article
Language:English
Subjects:
Alkylation
Palladium
Tppts
Two-phase system
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Summary:The regioselectivity of the reaction of ethyl acetoacetate on allylic carbonate in the presence of a catalyst prepared from Pd(OAc) 2 and P(C 6H 4- m-SO 3Na) 3 (or tppts) is not affected by the ratio Pd(OAc) 2/tppts, the nature of the nitrile, the relative amounts of water and nitrile or the temperature of the reaction. Under these conditions the alkylation of various carbonucleophiles having different p K a gave mainly the monoalkylated products in the case of acyclic carbonucleophiles and dialkylated products in the case of cyclic carbonucleophiles.
ISSN:1381-1169
1873-314X
DOI:10.1016/S1381-1169(96)00145-8