From Surf Wiki (app.surf) — the open knowledge base

Bis(triphenylphosphine)palladium chloride

| NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0

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: :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: :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.{{cite journal|journal=Acta Crystallogr.|year=1982|volume=B38|issue=10|pages=2679–2681

Applications

The complex is used as a pre-catalyst for a variety of coupling reactions.

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. The same catalyst is effective for the Sonogashira coupling.

References

"PdCl2(PPh3)2".
(1990). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-octadiene". Organic Syntheses.
Hiroshi Itatani. (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.
D. R. Coulson. (1972). "Inorganic Syntheses". [[Inorg. Synth.]].
G. Steyl. (2006). "''trans''-Dichlorobis(triphenylphosphine)palladium(II) dichloromethane solvate". [[Acta Crystallographica Section E.
J. Pons. (2008). "''trans''-Dichloridobis(triphenylphosphine)palladium(II)". [[Acta Crystallographica Section E.
A. Naghipour. (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". [[Journal of Organometallic Chemistry.
René Severin. (2010). "One-Pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes". J. Org. Chem..
Jacks, T. E.. (2004). "Development of a Scalable Process for CI-1034, an Endothelin Antagonist". Organic Process Research & Development.
Chinchilla, R.. (2007). "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry". Chem. Rev..

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

palladium-compounds triphenylphosphine-complexes chloro-complexes

Want to explore this topic further?

Ask Mako anything about Bis(triphenylphosphine)palladium chloride — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report