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

Uses

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), is a palladium catalyst used in chemical synthesis of various compounds.Is used in preparation of Nucleosides as Ectonucleotidase inhibitors.

Chemical Properties

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

Uses

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

Uses

suzuki reaction

Uses

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

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.

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

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

Synthesis

A method for the preparation of 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride II (dppfPdCl2) comprising the steps of:

(a) adding palladium chloride to concentrated hydrochloric acid, heating to 40-80C to dissolve, the amount of hydrochloric acid is 0.2-1.0 times the mass of palladium chloride, diluting with ethanol, the amount of ethanol is 10-50 times the mass of palladium chloride;

(b) bis-diphenylphosphinoferrocene (dppf) 3.0-5.0 times the mass of palladium chloride is added to a solution of tetrahydrofuran and heated to 40-80C until dissolved, and the amount of tetrahydrofuran is 20-30 times the mass of palladium chloride;

(c) the solution obtained in step (a) was added dropwise to the solution obtained in step (b), and after the dropwise addition was completed, it was held at 45-80C for 0.5-3h, and then cooled, filtered, washed, and dried in vacuum, to obtain 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride II red crystals.