Bis(triphenylphosphine)palladium(II) dichloride

Bis(triphenylphosphine)palladium(II) dichloride

Identifiers
CAS Registry Number	13965-03-2 Y
ChemSpider	75895 Y
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-2 Y Key: YNHIGQDRGKUECZ-UHFFFAOYSA-L Y 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-2 Key: YNHIGQDRGKUECZ-NUQVWONBAO
Jmol-3D images	Image
PubChem	6102075
SMILES [Pd+2].[Cl-].[Cl-].c3c(P(c1ccccc1)c2ccccc2)cccc3.c1ccccc1P(c2ccccc2)c3ccccc3
Properties
Molecular formula	C36H30Cl2P2Pd
Molar mass	701.90 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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:^[1]

PdCl₂ + 2 PPh₃ → PdCl₂(PPh₃)₂

The complex is an intermediate in the preparation of tetrakis(triphenylphosphine)palladium (Pd(PPh₃)₄):^[2]

PdCl₂(PPh₃)₂ + 2 PPh₃ + 2.5 N₂H₄ → Pd(PPh₃)₄ + 0.5 N₂ + 2 N₂H₅⁺Cl⁻

References

1. ↑ Norio Miyaura and Akira Suzuki (1993). "Palladium-catalyzed reaction of 1-alkenylboronates with vinylic halides: (1Z,3E)-1-Phenyl-1,3-octadiene". Org. Synth. ; Coll. 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.