1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex
[CAS# 95464-05-4]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex
• Molecular Formula: C₃₅H₃₀Cl₄FeP₂Pd
• Molecular Weight: 816.64
• CAS Registry Number: 95464-05-4
• EC Number: 619-128-9
• SMILES: c1ccc(cc1)P(c2ccccc2)C3=CC(C=C3)[Fe]C4C=CC(=C4)P(c5ccccc5)c6ccccc6.C(Cl)Cl.Cl[Pd]Cl

Properties

• Melting point: 266-283 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302+H312+H332-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Carcinogenicity	Carc.	2	H351
Specific target organ toxicity - single exposure	STOT SE	3	H336
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

1,1'-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex, commonly abbreviated as Pd(dppf)Cl2·CH2Cl2, was first synthesized and characterized in the field of organometallic chemistry at the end of the 20th century. The complex features a palladium(II) ion coordinated to two chloride ligands and a bidentate ligand, 1,1'-bis(diphenylphosphino)ferrocene (dppf). The discovery of the complex stems from the desire to exploit the unique properties of the ferrocene and palladium moieties to develop efficient catalysts for various organic transformations.

The main application of Pd(dppf)Cl2·CH2Cl2 is in catalytic cross-coupling reactions, particularly in Suzuki-Miyaura, Heck, and Sonogashira reactions. The ferrocene-based dppf ligand provides excellent stability and electronic properties to the palladium center, facilitating the coupling of organic substrates. The complex is widely used in synthetic organic chemistry for the construction of carbon-carbon and carbon-heteroatom bonds, which are essential for the synthesis of pharmaceuticals, agrochemicals, and materials science.

In the Heck reaction, Pd(dppf)Cl2·CH2Cl2 is used as a catalyst for the coupling of aryl halides or pseudohalides with olefins, enabling the formation of substituted olefins under mild reaction conditions. This process is important in the pharmaceutical industry for the modification of aromatic structures and the synthesis of biologically active compounds.

The Suzuki-Miyaura coupling promoted by Pd(dppf)Cl2·CH2Cl2 involves the coupling of aryl or vinyl boronic acids with aryl halides or pseudohalides. Due to its high efficiency and tolerance to various functional groups, this reaction is widely used in materials science for the synthesis of conjugated polymers, OLEDs (organic light-emitting diodes), and other electronic materials.

In addition to organic synthesis, this complex plays an important role in materials science, especially in the preparation of functionalized materials and catalysts for the production of fine chemicals. The robustness and versatility of Pd(dppf)Cl2·CH2Cl2 make it suitable for the development of new materials with customized properties, such as enhanced conductivity or optical properties.

Pd(dppf)Cl2·CH2Cl2 is also used in asymmetric synthesis, where the chiral environment provided by the dppf ligands around the palladium center enables the selective formation of chiral molecules. This application is critical in pharmaceutical research to produce enantiomerically pure compounds, which are often required for drug development to optimize efficacy and minimize side effects.

References

2002. Synthesis of bis[palladium(ii)] and bis[platinum(ii)] complexes containing chiral, linear quadridentate ligands with a P2N2 donor set. Journal of the Chemical Society, Dalton Transactions, (7).
DOI: 10.1039/B106861J

2017. Synthesis and redox reactions of bis(verdazyl)palladium complexes. Dalton Transactions, 46(37).
DOI: 10.1039/C7DT02646C