226703-30-6Relevant academic research and scientific papers
Heck-type benzylation of olefins with benzyl trifluoroacetates
Narahashi, Hirohisa,Yamamoto, Akio,Shimizu, Isao
, p. 348 - 349 (2004)
A new synthetic method for 1-aryl-2-alkenes from 1-olefins by benzylation treating with benzyl trifluoroacetates using palladium-catalyst is developed on the basis of oxidative addition of benzyl carboxylates to Pd(0) complexes to give benzyl(carboxylato)palladium(II) complexes with cleavage of benzyl-oxygen bond.
Oxidative addition of aryl and benzyl trifluoroacetates to zerovalent palladium complexes with two modes of C-O bond cleavage processes
Nagayama, Kazuhiro,Shimizu, Isao,Yamamoto, Akio
, p. 799 - 803 (2007/10/03)
The aryl trifluoroacetates oxidatively added to a zerovalent palladium complex 2a with acyl-O bond cleavage under mild conditions to give the corresponding trans-(aryloxo)(trifluoroacetyl)palladium complexes 3a-3c. But 4-nitrophenyl trifluoroacetate reacted with 2a to yield cis-[Pd(OC6H4-4- NO2)2(PMe3)2] 3d, which was produced with C-O bond activation followed by disproportionation reaction. In contrast, benzyl trifluoroacetates reacted with the Pd(0) complex with benzyl-O bond fission to form benzyl(trifluoroacetato)palladium complexes 4a-4d. Complexes 4a-4d are in equilibrium in solutions between trans and cis isomers, with the proportion of the cis isomer increasing in polar solvents. Palladium-catalyzed carbonylation of benzyl trifluoroacetate has been achieved in the presence of benzyl alcohol arid triethylamine to yield benzyl phenylacetate.
