[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

Description

Pd(dppf)Cl2 is a palladium catalyst that is commonly used in palladium catalyzed cross-couplings.

Chemical properties

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) is Red solid

The Uses of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) is used as a catalyst for Suzuki and Stile couplings.

The Uses of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

suzuki reaction

The Uses of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

Catalyst for C-C and C-N coupling reaction.

What are the applications of Application

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) may be used as an effective palladium catalyst in the following reactions:
Cross-coupling of sec-alkyl and n-alkyl Grignard reagents with high yield and selectivity.
Suzuki coupling of aryl boronic esters with [11C]methyl iodide to form functionalized [11C]toluene derivatives.
Kumada cross-coupling of 1,3,5-tribromobenzene with Grignard reagents to form star-shaped oligothiophenes.

Mechanism of action

[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (pd(dppf)cl2) catalysis has gained widespread use in industrial and academic synthetic chemistry laboratories as a powerful methodology for the formation of C-C and C-Heteroatom bonds.

R = usually sp2 hybridised carbon
X = usually I, Br, Cl or OTf
The nature of R' and M are dependant upon
the specic coupling being performed

Preparation

To a solution of the SM (2.0 g, 4.15 mmol) in MeOH (100 mL) was added Pd(dppf)Cl2-DCM (380 mg, 0.42 mmol) and TEA (838 mg, 8.30 mmol). The reaction mixture was stirred under an atmosphere of CO (20 atm) at 100 C for 24 h. After concentration, the residue was purified by chromatography (1:1 PE/EtOAc) to provide the product as a white solid. [1.1 g, 52%]