Bis(triphenylphosphine)palladium chloride

Bis(triphenylphosphine)palladium chloride
Identifiers
CAS Number	13965-03-2 ;
3D model (JSmol)	ionic form: Interactive image; coordination form: Interactive image;
ChemSpider	75895 ;
ECHA InfoCard	100.034.299
PubChem CID	6102075;
CompTox Dashboard (EPA)	DTXSID50930525 ;
	InChI InChI=1S/2C18H15P.2ClH.Pd/c21-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h21-15H;21H;/q;;;;+2/p-2 Key: YNHIGQDRGKUECZ-UHFFFAOYSA-L ; InChI=1/2C18H15P.2ClH.Pd/c21-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h21-15H;21H;/q;;;;+2/p-2 Key: YNHIGQDRGKUECZ-NUQVWONBAO;
	SMILES ionic form: [Pd+2].[Cl-].[Cl-].c3c(P(c1ccccc1)c2ccccc2)cccc3.c1ccccc1P(c2ccccc2)c3ccccc3; coordination form: Cl[Pd-2](Cl)([P+](c0ccccc0)(c0ccccc0)(c0ccccc0))[P+](c0ccccc0)(c0ccccc0)(c0ccccc0);
Properties
Chemical formula	PdCl2(PPh3)2
Molar mass	701.90 g·mol−1
Appearance	yellow powder
Melting point	260 °C (decomposed around 300 °C)
Solubility in water	insoluble
Solubility	soluble in chloroform, hexane, toluene, benzene, acetone
Hazards
NFPA 704 (fire diamond)	2 1 0
Flash point	181.7 °C
Related compounds
Related compounds	Bis(triphenylphosphine)platinum chloride
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. Many analogous complexes are known with different phosphine ligands.

Preparation and reactions

This compound may be prepared by treating palladium(II) chloride with triphenylphosphine:^[2]^[3]

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:^[4]

2 PdCl₂(PPh₃)₂ + 4 PPh₃ + 5 N₂H₄ → 2 Pd(PPh₃)₄ + N₂ + 4 N₂H₅⁺Cl⁻

Structure

Several crystal structures containing PdCl₂(PPh₃)₂ have been reported. In all of the structures, PdCl₂(PPh₃)₂ adopts a square planar coordination geometry and the trans isomeric form.^[5]^[6]^[7]^[8]

Applications

The complex is used as a pre-catalyst for a variety of coupling reactions.^[9]

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.^[10] The same catalyst is effective for the Sonogashira coupling.^[11]

References

^ "PdCl2(PPh3)2". ChemSpider. Retrieved 2 January 2024.
^ Norio Miyaura; Akira Suzuki (1990). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-octadiene". Organic Syntheses. 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 the American Oil Chemists' Society. 44: 147. doi:10.1007/BF02558176. S2CID 93580917.
^ D. R. Coulson (1972). "Tetrakis(triphenylphosphine)palladium(0)". Inorganic Syntheses. Vol. 13. pp. 121–124. doi:10.1002/9780470132449.ch23. ISBN 978-0-470-13244-9. {{cite book}}: |journal= ignored (help)
^ G. Ferguson; R. McCrindle; A. J. McAlees; M. Parvez (1982). "trans-Dichlorobis(triphenylphosphine)palladium(II)". Acta Crystallogr. B38 (10): 2679–2681. doi:10.1107/S0567740882009583.
^ G. Steyl (2006). "trans-Dichlorobis(triphenylphosphine)palladium(II) dichloromethane solvate". Acta Crystallogr. E. 62 (6): m1324 – m1325. doi:10.1107/S1600536806017521.
^ J. Pons; J. García-Antón; X. Solans; M. Font-Bardia; J. Ros (2008). "trans-Dichloridobis(triphenylphosphine)palladium(II)". Acta Crystallogr. E. 64 (Pt 5): m621. doi:10.1107/S1600536808008337. PMC 2961313. PMID 21202176.
^ A. Naghipour; A. Ghorbani-Choghamarani; H. Babaee; M. Hashemi; B. Notash (2017). "Crystal structure of a novel polymorph of trans-dichlorobis (triphenylphosphine) palladium (II) and its application as a novel, efficient and retrievable catalyst for the amination of aryl halides and stille cross-coupling reactions". J. Organomet. Chem. 841: 31–38. doi:10.1016/j.jorganchem.2016.10.002.
^ René Severin; Jessica Reimer; Sven Doye (2010). "One-Pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes". J. Org. Chem. 75 (10): 3518–352. doi:10.1021/jo100460v. PMID 20420397.
^ 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, Jason G.; Nanninga, Thomas N. (2004). "Development of a Scalable Process for CI-1034, an Endothelin Antagonist". Organic Process Research & Development. 8 (2): 201–212. doi:10.1021/op034104g.
^ Chinchilla, R.; Nájera, C. (2007). "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry". Chem. Rev. 107 (3): 874–922. doi:10.1021/cr050992x. PMID 17305399.

[chemspider-1] "PdCl2(PPh3)2". ChemSpider. Retrieved 2 January 2024.

[2] Norio Miyaura; Akira Suzuki (1990). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-octadiene". Organic Syntheses. 68: 130. doi:10.15227/orgsyn.068.0130.

[3] 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 the American Oil Chemists' Society. 44: 147. doi:10.1007/BF02558176. S2CID 93580917.

[4] D. R. Coulson (1972). "Tetrakis(triphenylphosphine)palladium(0)". Inorganic Syntheses. Vol. 13. pp. 121–124. doi:10.1002/9780470132449.ch23. ISBN 978-0-470-13244-9. {{cite book}}: |journal= ignored (help)

[5] G. Ferguson; R. McCrindle; A. J. McAlees; M. Parvez (1982). "trans-Dichlorobis(triphenylphosphine)palladium(II)". Acta Crystallogr. B38 (10): 2679–2681. doi:10.1107/S0567740882009583.

[6] G. Steyl (2006). "trans-Dichlorobis(triphenylphosphine)palladium(II) dichloromethane solvate". Acta Crystallogr. E. 62 (6): m1324 – m1325. doi:10.1107/S1600536806017521.

[7] J. Pons; J. García-Antón; X. Solans; M. Font-Bardia; J. Ros (2008). "trans-Dichloridobis(triphenylphosphine)palladium(II)". Acta Crystallogr. E. 64 (Pt 5): m621. doi:10.1107/S1600536808008337. PMC 2961313. PMID 21202176.

[8] A. Naghipour; A. Ghorbani-Choghamarani; H. Babaee; M. Hashemi; B. Notash (2017). "Crystal structure of a novel polymorph of trans-dichlorobis (triphenylphosphine) palladium (II) and its application as a novel, efficient and retrievable catalyst for the amination of aryl halides and stille cross-coupling reactions". J. Organomet. Chem. 841: 31–38. doi:10.1016/j.jorganchem.2016.10.002.

[9] René Severin; Jessica Reimer; Sven Doye (2010). "One-Pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes". J. Org. Chem. 75 (10): 3518–352. doi:10.1021/jo100460v. PMID 20420397.

[10] 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, Jason G.; Nanninga, Thomas N. (2004). "Development of a Scalable Process for CI-1034, an Endothelin Antagonist". Organic Process Research & Development. 8 (2): 201–212. doi:10.1021/op034104g.

[11] Chinchilla, R.; Nájera, C. (2007). "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry". Chem. Rev. 107 (3): 874–922. doi:10.1021/cr050992x. PMID 17305399.

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Bis(triphenylphosphine)palladium chloride

Preparation and reactions

Structure

Applications

See also

References

Information related to Bis(triphenylphosphine)palladium chloride

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