Wednesday, February 29, 2012

What is Tetrakis(triphenylphosphine)palladium(0) used for?


Tetrakis(triphenylphosphine)palladium(0) is the chemical compound Pd[P(C6H5)3]4, often abbreviated Pd(PPh3)4, or even PdP4. It is a bright yellow crystalline solid that becomes brown upon decomposition in air.
Preparation
Tetrakis(triphenylphosphine)palladium(0) was first prepared by Lamberto Malatesta and his group in Milan in the 1960s by reduction of sodium chloropalladate with hydrazine in the presence of the phosphine. It is commercially available, but can be prepared in two steps from Pd(II) precursors.
Applications of Tetrakis(triphenylphosphine)palladium(0)
Pd(PPh3)4 is widely used as a catalyst for palladium-catalyzed coupling reactions. Prominent applications include the Heck reaction, Suzuki coupling, Stille coupling, Sonogashira coupling, and Negishi coupling. These processes begin with two successive ligand dissociations followed by the oxidative addition of an aryl halide to the Pd(0) center:Pd(PPh3)4 + ArBr → PdBr(Ar)(PPh3)2 + 2 PPh3
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