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Bis(triphenylphosphine)palladium chloride

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Bis(triphenylphosphine)palladium chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.299 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2Key: YNHIGQDRGKUECZ-UHFFFAOYSA-L
  • InChI=1/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2Key: YNHIGQDRGKUECZ-NUQVWONBAO
SMILES
  • ...c3c(P(c1ccccc1)c2ccccc2)cccc3.c1ccccc1P(c2ccccc2)c3ccccc3
Properties
Chemical formula C36H30Cl2P2Pd
Molar mass 701.90 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Bis(triphenylphosphine)palladium(II) dichloride is a coordination compound of palladium containing two triphenylphosphine and two chloride ligands. This yellow complex is often used for palladium-catalyzed coupling reactions, e.g. the Sonogashira–Hagihara reaction. The complex is square planar. Both cis and trans isomers are known.

Commercially available, this compound may be prepared by reacting palladium(II) chloride with triphenylphosphine:

PdCl2 + 2 PPh3 → PdCl2(PPh3)2

The complex is an intermediate in the preparation of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4):

PdCl2(PPh3)2 + 2 PPh3 + 2.5 N2H4 → Pd(PPh3)4 + 0.5 N2 + 2 N2H5Cl

References

  1. Norio Miyaura and Akira Suzuki (1993). "Palladium-catalyzed reaction of 1-alkenylboronates with vinylic halides: (1Z,3E)-1-Phenyl-1,3-octadiene". Organic Syntheses; Collected Volumes, vol. 8, p. 532.
  2. D. R. Coulson; Satek, L. C.; Grim, S. O. (1972). "23. Tetrakis(triphenylphosphine)palladium(0)". Inorg. Synth. 13: 121. doi:10.1002/9780470132449.ch23.
Palladium compounds
Pd(0)
Organopalladium(0) compounds
  • Pd2((C6H5C2H2)2CO)3
    • Pd(II)
    Organopalladium(II) compounds
  • ((CH2)2CHPdCl)2
  • (C5H5)Pd(C3H5)
    • Pd(II,IV)
    Pd(IV)
    Pd(VI)
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    Bis(triphenylphosphine)palladium chloride Add topic