522606-71-9Relevant academic research and scientific papers
Mechanism of the Stille reaction catalyzed by palladium ligated to arsine ligand: PhPdl(AsPh3)(DMF) is the species reacting with vinylstannane in DMF
Amatore, Christian,Bahsoun, Ali A.,Jutand, Anny,Meyer, Gilbert,Ndedi Ntepe, Alexandre,Ricard, Louis
, p. 4212 - 4222 (2003)
The kinetics of the reaction of PhPdI(AsPh3)2 (formed via the fast oxidative addition of Phl with Pd0(AsPh3)2) with a vinyl stannane CH2=CH-Sn(n-Bu)3 has been investigated in DMF. This reaction (usually called transmetalation step) is the prototype of the rate determining second step of the catalytic cycle of Stille reactions. It is established here that the transmetalation proceeds through PhPdI(AsPh3)(DMF), generated by the dissociation of one ligand AsPh3 from PhPdI(AsPh3)2. PhPdI(AsPh3)(DMF) is the reactive species, which leads to styrene through its reaction with CH2=CH-SnBu3. Consequently, in DMF, the overall nucleophilic attack mainly proceeds via a mechanism involving PhPdI(AsPh3)(DMF) as the central reactive complex and not PhPdI(AsPh3)2. The dimer [Ph2Pd2(μ2-I)2 (AsPh3)2] has been independently synthesized and characterized by its X-ray structure. In DMF, this dimer dissociates quantitatively into PhPdI(AsPh3)(DMF), which reacts with CH2=CH-SnBu3. The rate constant for the reaction of PhPdI-(AsPh3)(DMF) with CH2=CH-SnBu3 has been determined in DMF for each situation and was found to be comparable.
