- Tetrakis(triphenylphosphine)palladium(0)
Chembox new
Name = Tetrakis(triphenylphosphine)palladium(0)
ImageFile = Tetrakis(triphenylphosphine)palladium(0)-3D-sticks.png
ImageName = 3D model of the tetrakis(triphenylphosphine)palladium(0) molecule
ImageFile1 = Tetrakis(triphenylphosphine)palladium(0).jpg
ImageName1 = Tetrakis(triphenylphosphine)palladium(0)
IUPACName = Tetrakis(triphenylphosphane)palladium(0)
OtherNames = TPP palladium(0)
Section1 = Chembox Identifiers
CASNo = 14221-01-3
RTECS = Unregistered
Section2 = Chembox Properties
Formula = carbon72hydrogen60phosphorus4palladium
MolarMass = 1155.56 g/mol
Appearance = Bright yellow crystals
Density = ? g/cm3, ?
Solubility = Insoluble
MeltingPt = decomposes around 115 °C
Section3 = Chembox Structure
MolShape =tetrahedral
Coordination = fourtriphenylphosphine unidentate
ligand s attached to a central Pd(0)
atom in atetrahedral geometry
CrystalStruct =
Dipole = 0 D
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = PPh3 is an irritant
NFPA-H = 2
NFPA-F = 1
NFPA-R =
RPhrases = n/a
SPhrases = S22, S24/25
Section8 = Chembox Related
Function = complexes
OtherFunctn = chlorotris(triphenylphosphine)rhodium(I)tris(dibenzylideneacetone)dipalladium(0)
OtherCpds =triphenylphosphine 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 yellowcrystalline solid that becomes brown upon decomposition in air.Preparation, structure, and properties
This complex is prepared in two steps from Pd(II) precursors::PdCl2 + 2 PPh3 → "cis"-PdCl2(PPh3)2:"cis"-PdCl2(PPh3)2 + 2 PPh3 + 2.5 N2H4 → Pd(PPh3)4 + 0.5 N2 + 2 N2H5+Cl-
Reductant s other thanhydrazine can be employed.The four P atoms are at the corners of a tetrahedron surrounding the palladium(0) center. This structure is typical for four-coordinate 18e complexes. [C. Elschenbroich, A. Salzer ”Organometallics : A Concise Introduction” (2nd Ed) (1992) from Wiley-VCH: Weinheim. ISBN 3-527-28165-7] The corresponding complexes Ni(PPh3)4 and Pt(PPh3)4 are also well known. Such complexes reversibly dissociate PPh3 ligands in solution, releasing the 16e M(PPh3)3. Thus, reactions attributed to Pd(PPh3)4 in fact arise from Pd(PPh3)3 or even Pd(PPh3)2.
If the tetrakis(triphenylphosphine)palladium (0) is an orange brown, triturate with methanol and filter to give the desired yellow powder. Store under nitrogen in the fridge.
Applications
Pd(PPh3)4 is widely used as a
catalyst forcoupling reaction s. [Homogeneous Catalysis: Understanding the Art” by P. W. van Leeuwen, Springer; 2005. ISBN 1-4020-3176-9] Prominent applications include theHeck reaction andSuzuki coupling . These processes begin with theoxidative addition of an aryl halide to the Pd(0) center::Pd(PPh3)4 + ArBr → PdBr(Ar)(PPh3)2 + 2 PPh3References
External links
* [http://www.chemexper.com/index.shtml?main=http://www.chemexper.com/search/cas/14221-01-3.html ChemExper Chemicals database]
* [http://www.sciencelab.com/page/S/PVAR/10427/SLT3655 Science lab product sheet]
* [http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/pph3.noble.metal.catalysts.html D.R. Coulson, "Tetrakis(triphenylphosphine)palladium(0)", Inorg. Synth., No 21]
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