ChemicalBook Product Catalog Organic Chemistry Organometallic compounds Organic palladium [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

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

Product Name[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)
CAS72287-26-4
MFC34H28Cl2FeP2Pd
MW731.7
EINECS460-040-3
MOL File72287-26-4.mol

Chemical Properties

Melting point	275-280 °C(lit.)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	Soluble in dichloromethane.
form	powder
color	red to very dark red
Stability	Hygroscopic
InChI	InChI=1S/2C17H11P.2ClH.Fe.Pd/c21-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;;;;/h21-6,9-12,18H;2*1H;;/q;;;;+2;/p-2
InChIKey	LMSWLYFMTLONFK-UHFFFAOYSA-L
SMILES	[Cl-][Pd+2]1(P(C2C=CC=CC=2)(C2C=CC=CC=2)[C-]23C4=C5C6=C2[Fe+2]27893456C3C2=C7[C-]8(C9=3)P1(C1C=CC=CC=1)C1C=CC=CC=1)[Cl-]

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	20/21/22-36/37/38-40
Safety Statements	23-24/25-26-36/37
WGK Germany	3
TSCA	No
HazardClass	IRRITANT
HS Code	28439000
Storage Class	6.1D - Non-combustible acute toxic Cat.3 toxic hazardous materials or hazardous materials causing chronic effects
Hazard Classifications	Carc. 1B Inhalation

Usage And Synthesis

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.

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

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.