Bis(triphenylphosphine)palladium chloride

Bis(triphenylphosphine)palladium chloride

Identifiers
CAS Number	13965-03-2 Y
3D model (Jmol)	Interactive image
ChemSpider	75895 Y
ECHA InfoCard	100.034.299
PubChem	6102075
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
SMILES [Pd+2].[Cl-].[Cl-].c3c(P(c1ccccc1)c2ccccc2)cccc3.c1ccccc1P(c2ccccc2)c3ccccc3
Properties
Chemical formula	C36H30Cl2P2Pd
Molar mass	701.90 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bis(triphenylphosphine)palladium chloride is a coordination compound of palladium containing two triphenylphosphine and two chloride ligands. It is a yellow solid that is soluble in some organic solvents. It is used for palladium-catalyzed coupling reactions, e.g. the Sonogashira–Hagihara reaction. The complex is square planar. Both cis and trans isomers are known. Many analogous complexes are known with different phosphine ligands.

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.