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Sku CI31477_1_G
Chem Impex
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Product Information

Product Name
1,1'-Bis(diphenylphosphino)ferrocenepalladium(II) dichloride dichloromethane adduct
Brand Name
Chem Impex
Product Number
31477
CAS
95464-05-4
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
51341998
IUPAC Name
bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloromethane;dichloropalladium;iron(2+)
InChI Key
SNRCKKQHDUIRIY-UHFFFAOYSA-L
SMILES
CH-1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.CH-1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C(Cl)Cl.ClPdCl.Fe+2

Description

🧑‍🔬 Catalyzing Cross-Coupling Reactions
This is its most central application. It is extensively used to catalyze a variety of cross-coupling reactions that form carbon-carbon and carbon-heteroatom bonds, making it an indispensable tool for constructing complex organic molecules.

  • Suzuki-Miyaura Coupling: Catalyzes the coupling of arylboronic acids with aryl halides, serving as one of the most important methods for synthesizing biaryl compounds, which are common structures in pharmaceuticals and materials.

  • Stille Coupling: Catalyzes the coupling of organotin compounds with halides.

  • Negishi Coupling: Catalyzes the coupling of organozinc compounds with halides.

  • Buchwald-Hartwig Amination: Catalyzes the coupling of aryl halides with amines, a key method for constructing arylamine compounds used in the synthesis of drugs and materials.

🧪 Other Catalytic Transformations
Beyond the coupling reactions mentioned above, Pd(dppf)Cl₂ is also an effective catalyst for various other transformations.

  • Borylation of Aryl Halides: Introduces boronate ester groups onto aromatic rings, providing precursors for further coupling reactions.

  • Carbonylation Reactions: Catalyzes reactions that introduce carbonyl groups.

  • Domino/Tandem Reactions: Used for the one-step construction of complex polycyclic molecules, such as in the synthesis of polyheterocycles.

⚛️ Synthetic Building Block and Ligand Precursor
The compound itself is a stable, well-defined organometallic complex. It can serve as a precursor to generate the actual catalytically active zero-valent palladium species (Pd(0)) in situ, or as a source of the bisphosphine ligand (dppf). Researchers also utilize its well-defined structure for spectroscopic studies to investigate catalytic reaction mechanisms