779340-39-5Relevant academic research and scientific papers
Rate and mechanism of the reaction of (E)-PhCH=CH-CH(Ph)-OAc with palladium(0) complexes in allylic substitutions
Amatore, Christian,Bahsoun, Ali A.,Jutand, Anny,Mensah, Laure,Meyer, Gilbert,Ricard, Louis
, p. 1569 - 1577 (2008/10/09)
The reaction of (E)-1,3-diphenyl-3-acetoxyprop-1-ene, PhCH=CH-CH(Ph)-OAc, with palladium(0) complexes Pd0L2, generated from Pd 0(PPh3)4 or Pd0(dba)2 + 2L (L = PPh3 or
Allylic substitution mediated by water and palladium: Unusual role of a palladium(II) catalyst and ESI-MS analysis
Chevrin, Carole,Le Bras, Jean,Henin, Francoise,Muzart, Jacques,Pla-Quintana, Anna,Roglans, Anna,Pleixats, Roser
, p. 4796 - 4799 (2008/10/09)
Allylic substitution of PhCH(OAc)CH=CHPh by CH2(COMe) 2 in a basic MeOH/H2O mixture could be achieved in the absence of a palladium catalyst and lead to a mixture of PhCH(CH(COMe) 2)CH=CHPh and PhCH(OMe)CH=CHPh in 40% and 55% yields, respectively. The process is induced by water, and nucleophilic attack addition occurred on a stabilized carbocation as the intermediate. Addition of a catalytic amount of PdCl2(CH3CN)2 did not accelerate the reaction but improved the selectivity, and PhCH(CH(COMe)2)CH=CHPh was then obtained in 92% yield while PhCH(OMe)-CH=CHPh was observed in trace amounts. An ESI-MS analysis of the reaction mixture led us to assume that a palladium acetylacetonate complex is involved in the formation of PhCH(CH(COMe) 2)CH=CHPh.
