Bis(triphenylphosphine)palladium(II) dichloride

Bis(triphenylphosphine)palladium(II) dichloride
Identifiers
CAS number	13965-03-2 Y
PubChem	6102075
ChemSpider	75895 Y
Jmol-3D images	Image 1
SMILES [Pd+2].[Cl-].[Cl-].c3c(P(c1ccccc1)c2ccccc2)cccc3.c1ccccc1P(c2ccccc2)c3ccccc3
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
Properties
Molecular formula	C36H30Cl2P2Pd
Molar mass	701.9 g mol−1
Y dichloride (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0532 ; Coll. Vol. 8: 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.