Tetrakis(triphenylphosphine)palladium(0) (sometimes called quatrotriphenylphosphine palladium) is the chemical compound [Pd(P(C6H5)3)4], often abbreviated Pd(PPh3)4, or rarely PdP4. It is a bright yellow crystalline solid that becomes brown upon decomposition in air.
The four phosphorusatoms are at the corners of a tetrahedron surrounding the palladium(0) center. This structure is typical for four-coordinate 18 e− complexes.[2] The corresponding complexes Ni(PPh3)4 and Pt(PPh3)4 are also well known. Such complexes reversibly dissociate PPh3ligands in solution, so reactions attributed to Pd(PPh3)4 often in fact arise from Pd(PPh3)3 or even Pd(PPh3)2.
Preparation
Tetrakis(triphenylphosphine)palladium(0) was first prepared by Lamberto Malatesta et al. in the 1950s by reduction of sodium chloropalladate with hydrazine in the presence of the phosphine.[3] It is commercially available, but can be prepared in two steps from Pd(II) precursors:
Both steps may be carried out in a one-pot reaction, without isolating and purifying the PdCl2(PPh3)2 intermediate.[4]Reductants other than hydrazine can be employed. The compound is sensitive to air, but can be purified by washing with methanol to give the desired yellow powder. It is usually stored cold under argon.
^Elschenbroich, C.; Salzer, A. (1992). Organometallics: A Concise Introduction (2nd ed.). Weinheim: Wiley-VCH. ISBN3-527-28165-7.
^Malatesta, L.; Angoletta, M. (1957). "Palladium(0) compounds. Part II. Compounds with triarylphosphines, triaryl phosphites, and triarylarsines". J. Chem. Soc.1957: 1186. doi:10.1039/JR9570001186.
^Coulson, D. R.; Satek, L. C.; Grim, S. O. (1972). Tetrakis(triphenylphosphine)palladium(0). Inorg. Synth. Inorganic Syntheses. Vol. 13. p. 121. doi:10.1002/9780470132449.ch23. ISBN978-0-470-13244-9.
^Van Leeuwen, P. W. (2005). Homogeneous Catalysis: Understanding the Art. Springer. ISBN1-4020-3176-9.
January 07, 2023
tetrakis, triphenylphosphine, palladium, sometimes, called, quatrotriphenylphosphine, palladium, chemical, compound, c6h5, often, abbreviated, pph3, rarely, pdp4, bright, yellow, crystalline, solid, that, becomes, brown, upon, decomposition, namesiupac, name, . Tetrakis triphenylphosphine palladium 0 sometimes called quatrotriphenylphosphine palladium is the chemical compound Pd P C6H5 3 4 often abbreviated Pd PPh3 4 or rarely PdP4 It is a bright yellow crystalline solid that becomes brown upon decomposition in air Tetrakis triphenylphosphine palladium 0 NamesIUPAC name Tetrakis triphenylphosphane palladium 0 Other names TPP palladium 0 IdentifiersCAS Number 14221 01 3 Y3D model JSmol Interactive imageChemSpider 10152942ECHA InfoCard 100 034 609EC Number 238 086 9PubChem CID 11979704UNII N9O1RWZ93J YCompTox Dashboard EPA DTXSID9065732InChI InChI 1S 4C18H15P Pd c4 1 4 10 16 11 5 1 19 17 12 6 2 7 13 17 18 14 8 3 9 15 18 h4 1 15H Key NFHFRUOZVGFOOS UHFFFAOYSA NSMILES Pd P c1ccccc1 c1ccccc1 c1ccccc1 P c1ccccc1 c1ccccc1 c1ccccc1 P c1ccccc1 c1ccccc1 c1ccccc1 P c1ccccc1 c1ccccc1 c1ccccc1PropertiesChemical formula C 72H 60P 4PdMolar mass 1155 59 g mol 1Appearance Bright yellow to chartreuse crystalsMelting point decomposes around 115 CSolubility in water InsolubleStructureCoordination geometry four triphenylphosphine monodentate ligands attached to a central Pd 0 atom in a tetrahedral geometryMolecular shape tetrahedralDipole moment 0 DHazardsGHS labelling 1 PictogramsSignal word WarningHazard statements H302 H317 H413Precautionary statements P261 P264 P270 P272 P273 P280 P301 P312 P302 P352 P330 P333 P313 P363 P501NFPA 704 fire diamond 21Related compoundsRelated complexes chlorotris triphenylphosphine rhodium I tris dibenzylideneacetone dipalladium 0 Tetrakis triphenylphosphine platinum 0 Tetrakis triphenylphosphine nickel 0 Related compounds triphenylphosphineExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Structure and properties 2 Preparation 3 Applications 4 ReferencesStructure and properties EditThe four phosphorus atoms are at the corners of a tetrahedron surrounding the palladium 0 center This structure is typical for four coordinate 18 e complexes 2 The corresponding complexes Ni PPh3 4 and Pt PPh3 4 are also well known Such complexes reversibly dissociate PPh3 ligands in solution so reactions attributed to Pd PPh3 4 often in fact arise from Pd PPh3 3 or even Pd PPh3 2 Preparation EditTetrakis triphenylphosphine palladium 0 was first prepared by Lamberto Malatesta et al in the 1950s by reduction of sodium chloropalladate with hydrazine in the presence of the phosphine 3 It is commercially available but can be prepared in two steps from Pd II precursors PdCl2 2 PPh3 PdCl2 PPh3 2 PdCl2 PPh3 2 2 PPh3 5 2 N2H4 Pd PPh3 4 1 2 N2 2 N2H5ClBoth steps may be carried out in a one pot reaction without isolating and purifying the PdCl2 PPh3 2 intermediate 4 Reductants other than hydrazine can be employed The compound is sensitive to air but can be purified by washing with methanol to give the desired yellow powder It is usually stored cold under argon Applications EditPd PPh3 4 is widely used as a catalyst for palladium catalyzed coupling reactions 5 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 PPh3References Edit Tetrakis triphenylphosphine palladium pubchem ncbi nlm nih gov Elschenbroich C Salzer A 1992 Organometallics A Concise Introduction 2nd ed Weinheim Wiley VCH ISBN 3 527 28165 7 Malatesta L Angoletta M 1957 Palladium 0 compounds Part II Compounds with triarylphosphines triaryl phosphites and triarylarsines J Chem Soc 1957 1186 doi 10 1039 JR9570001186 Coulson D R Satek L C Grim S O 1972 Tetrakis triphenylphosphine palladium 0 Inorg Synth Inorganic Syntheses Vol 13 p 121 doi 10 1002 9780470132449 ch23 ISBN 978 0 470 13244 9 Van Leeuwen P W 2005 Homogeneous Catalysis Understanding the Art Springer ISBN 1 4020 3176 9 Retrieved from https en wikipedia org w index php title Tetrakis triphenylphosphine palladium 0 amp oldid 1059570270, wikipedia, wiki, book, books, library,
