Bis(triphenylphosphine)palladium chloride
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| Identifiers | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.034.299 |
PubChem CID |
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| 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 | |
| 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). | |
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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, 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]
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
- ↑ Norio Miyaura and Akira Suzuki (1990). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-octadiene". 68: 130. doi:10.15227/orgsyn.068.0130.
- ↑ Hiroshi Itatani, J.C.Bailar (1967). "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. doi:10.1007/BF02558176.
- ↑ D. R. Coulson (1972). "Tetrakis(triphenylphosphine)palladium(0)". Inorg. Synth. 13: 121. doi:10.1002/9780470132449.ch23.
- ↑ G. Ferguson, R. McCrindle, A. J. McAlees and M. Parvez (1982). "trans-Dichlorobis(triphenylphosphine)palladium(II)". Acta Crystallogr. B38: 2679–2681. doi:10.1107/S0567740882009583.
- ↑ René Severin, Jessica Reimer, Sven Doye (2010). "One-Pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes". J. Org. Chem. 10: 3518–352. doi:10.1021/jo100460v.
- ↑ Jacks, T. E.; Belmont, Daniel T.; Briggs, Christopher A.; Horne, Nicole M.; Kanter, Gerald D.; Karrick, Greg L.; Krikke, James J.; McCabe, Richard J.; Mustakis; Nanninga, Thomas N. (2004). "Development of a Scalable Process for CI-1034, an Endothelin Antagonist". Organic Process Research & Development. 8: 201–212. doi:10.1021/op034104g.
- ↑ Chinchilla, R.; Nájera, C. (2007). "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry". Chem. Rev. 107: 874–922. doi:10.1021/cr050992x.