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Bis(triphenylphosphine)palladium chloride

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Bis(triphenylphosphine)palladium chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.299 Edit this at Wikidata
  • 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 checkY
    Key: YNHIGQDRGKUECZ-UHFFFAOYSA-L checkY
  • 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
  • [Pd+2].[Cl-].[Cl-].c3c(P(c1ccccc1)c2ccccc2)cccc3.c1ccccc1P(c2ccccc2)c3ccccc3
Properties
C36H30Cl2P2Pd
Molar mass 701.90 g·mol−1
Appearance yellow powder
Melting point 260°C (decomposed around 300°C)
Insoluble in water, acetone, ether, Carbon tetrachloride and n-heptane // Soluble in CHCl3 and CH2Cl2, Chloroform (Slightly), Methanol (Slightly, Heated)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 181.7°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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, but the cis isomer is more common. Many analogous complexes are known with different phosphine ligands. The oxidative addition initially forms the cis–palladium complex, which rapidly isomerizes to the trans-complex.

Preparation and reactions

This compound may be prepared by treating palladium(II) chloride with triphenylphosphine:[1][2]

PdCl2 + 2 PPh3 PdCl2(PPh3)2

Upon reduction with hydrazine in the presence of excess triphenylphosphine, the complex is a precursor to tetrakis(triphenylphosphine)palladium (Pd(PPh3)4):[3]

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

Structure

The two different configuration (cis/trans) of the compound have planner structure.[4] However, the cis configuration has slightly distorted planar structure because of steric hindrance.

Applications

The complex is used as a catalyze for a variety of coupling reactions.[5]

One-pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes.

The Suzuki reaction was once limited by high levels of catalyst and the limited availability of boronic acids. Replacements for halides were also found, increasing the number of coupling partners for the halide or pseudohalide as well. Using bis(triphenylphosphine)palladium chloride as the catalyst, triflates and boronic acids have been coupled on an 80 kilogram scale in good yield.[6] The same catalyst is effective for the Sonogashira reaction.[7]

References

  1. ^ "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-octadiene". 68. 1990: 130. doi:10.15227/orgsyn.068.0130. {{cite journal}}: Cite journal requires |journal= (help); Cite uses deprecated parameter |authors= (help)
  2. ^ "Homogeneous Catalysis in the Reactions of olefinic Substances. V.Hydrogenation of Soybean Oil Methyl Ester with Triphenylphosphine and Triphenylarsine Palladium Catalysts". Journal of American Oil Chemists Society. 44: 147. 1967. doi:10.1007/BF02558176. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  3. ^ D. R. Coulson (1972). "Tetrakis(triphenylphosphine)palladium(0)". Inorg. Synth. 13: 121. doi:10.1002/9780470132449.ch23.
  4. ^ "trans-Dichlorobis(triphenylphosphine)palladium(II)". Acta Crystallogr. B38: 2679–2681. 1982. doi:10.1107/S0567740882009583. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  5. ^ "One-Pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes". J. Org. Chem. 10: 3518–352. 2010. doi:10.1021/jo100460v. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  6. ^ "Development of a Scalable Process for CI-1034, an Endothelin Antagonist". Organic Process Research & Development. 8: 201–212. 2004. doi:10.1021/op034104g. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  7. ^ "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry". Chem. Rev. 107: 874–922. 2007. doi:10.1021/cr050992x. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
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