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

✍ Scribed by Silvana Sigismondi; Denis Sinou

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 665 KB
• Volume: 116
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/s1381-1169(96)00145-8

✦ Synopsis

The regioselectivity of the reaction of ethyl acetoacetate on allylic carbonate in the presence of a catalyst prepared from Pd(OAc), and P(C,H,-m-SO,Na), (or tppts) is not affected by the ratio Pd(OAc),/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 pK, gave mainly the monoalkylated products in the case of acyclic carbonucleophiles and dialkylated products in the case of cyclic carbonucleophiles.