215788-65-1

Basic information

• Product Name: 1,1 bis(di-isopropylphosphine)ferrocene palladium dichloride
• Synonyms: PdCl2(dippf);1,1 bis(di-isopropylphosphine)ferrocene palladium dichloride;1,1μ-Bis(di-isopropylphosphino)ferrocene palladium dichloride;Dichloro[1,1'-bis(di-i-propylphosphino)ferrocene]palladium (II), 99%;1,1′-Bis(di-isopropylphosphino)ferrocene palladium dichloride 98%;Dichloro[1,1'-bis(di-i-propylphosphino)ferrocene]palladiuM(II),99%;[1,1'-Bis(diisopropylphosphino)ferrocene]dichloropalladium;Dichloro(1,1'-bis(diisopropylphosphino)ferrocene)palladium
• CAS NO: 215788-65-1
• Molecular Formula: C₂₂H₃₆Cl₂FeP₂Pd
• Molecular Weight: 595.645
• Product Categories: Pd
• Mol File: 215788-65-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 282-287 °C
• Appearance: yellow-orange/solid
• Storage Temp.: ?20°C
• CAS DataBase Reference: 1,1 bis(di-isopropylphosphine)ferrocene palladium dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1 bis(di-isopropylphosphine)ferrocene palladium dichloride(215788-65-1)
• EPA Substance Registry System: 1,1 bis(di-isopropylphosphine)ferrocene palladium dichloride(215788-65-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 215788-65-1(Hazardous Substances Data)

Usage

Reaction

Palladium-catalyzed P-C bond formation between diphenylphosphine and ortho-substituted aryl bromides. Deoxygenation of pyridine N-oxides by palladium-catalyzed oxidation of trialkylamines Air-stable catalyst useful in challenging Suzuki coupling reactions.

Chemical Properties

Orange yellow crystals

Synthetic route

1,1'-bis(diisopropylphosphino)ferrocene (97239-80-0) + palladium dichloride → dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1)

Conditions	Yield
With HCl In diethyl ether; ethanol PdCl2 suspn. in EtOH treated with conc. HCl, stirred at 50°C for30 min, filtered, Fe complex (1 equiv.) soln. in Et2O added at 20°C, stirred for 10 min; crystd. at -35°C, filtered, washed (H2O), dried (vac.); elem. anal.;	38%

dichloromethane (75-09-2) + dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + 4-mercaptopyridine-3-carboxylic acid (18103-73-6) → [1,1'-bis(diisopropylphosphino)ferrocene]palladium(II) thionicotinate *0.5 CH2Cl2

Conditions	Yield
With triethylamine In dichloromethane byproducts: (C2H5)3NHCl; (N2), mixed, stirred at room temp. for 3 h; filtered, pptd.(hexane), recrystd.(CH2Cl2/hexane), elem. anal., IR, NMR,MAS, XRD;	79%

dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + Thiosalicylic acid (147-93-3) → [1,1'-bis(diisopropylphosphino)ferrocene]palladium(II) thiosalicylate (403609-52-9)

Conditions	Yield
With triethylamine In dichloromethane byproducts: (C2H5)3NHCl; (N2), mixed, stirred at room temp. for 3 h; filtered, pptd.(hexane), recrystd.(CH2Cl2/hexane), elem. anal., IR, NMR,MAS, XRD;	68%

ortho-mercaptophenol (1121-24-0) + dichloromethane (75-09-2) + dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) → [1,1'-bis(diisopropylphosphino)ferrocene]palladium(II) 2-mercaptophenolate * 0.5CH2Cl2

Conditions	Yield
With triethylamine In dichloromethane byproducts: (C2H5)3NHCl; (N2), mixed, stirred at room temp. for 3 h; filtered, pptd.(hexane), recrystd.(CH2Cl2/hexane), elem. anal., IR, NMR,MAS, XRD;	70%

3,4-dimercaptotoluene (496-74-2) + dichloromethane (75-09-2) + dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) → [1,1'-bis(diisopropylphosphino)ferrocene]palladium(II) 3,4-toluenedithiolate * CH2Cl2 (403609-49-4)

Conditions	Yield
With triethylamine In dichloromethane byproducts: (C2H5)3NHCl; (N2), mixed, stirred at room temp. for 3 h; filtered, pptd.(hexane), recrystd.(CH2Cl2/hexane), elem. anal., IR, NMR,MAS, XRD;	56%

3,6-dichlorobenzene-1,2-dithiol (87314-49-6) + dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) → [1,1'-bis(diisopropylphosphino)ferrocene]palladium(II) 3,6-dichloro-1,2-benzenedithiolate (403609-50-7)

Conditions	Yield
With triethylamine In dichloromethane byproducts: (C2H5)3NHCl; (N2), mixed, stirred at room temp. for 3 h; filtered, pptd.(hexane), recrystd.(CH2Cl2/hexane), elem. anal., IR, NMR,MAS, XRD;	49%

dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + 1,2-benzenedithiole (17534-15-5) → [1,1'-bis(diisopropylphosphino)ferrocene]palladium(II) 1,2-benzenedithiolate (403609-47-2)

Conditions	Yield
With triethylamine In dichloromethane byproducts: (C2H5)3NHCl; (N2), mixed, stirred at room temp. for 3 h; filtered, pptd.(hexane), recrystd.(CH2Cl2/hexane), elem. anal., IR, NMR,MAS, XRD;	52%

dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1) → [Pd(dippf)(μ-Cl)]2[tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]2

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	69%

dichloromethane (75-09-2) + dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + thiophenol (108-98-5) → [ferrocene-1,1'-diylbis(diisopropylphosphine-P)]bis(phenylthio)palladium(II)*CH2Cl2

Conditions	Yield
With Et3N In toluene byproducts: Et3NHCl; under N2, Pd-complex was added to toluene soln. of thiophenol; Et3NHCl was filtered off, filtrate was evapd. to dryness, residue was recrystd. from CH2Cl2/hexane (1:2), hexane was layered onto CH2Cl2 soln., slow diffusion of hexane at 258 K; elem. anal.;	68%

bis(acetonitrile)dichloroplatinum(II) (13869-38-0, 21264-32-4, 13869-42-6) + dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) → [Pt(dippf)Cl2] (635727-62-7)

Conditions	Yield
In dichloromethane under Ar atm. mixt. (PtCl2(MeCN)2) and dippf in CH2Cl2 was stirred at room temp. for 1 h; soln. was concd., hexane was added, ppt. was filtered, washed with etherand dried in vacuo; elem. anal.;	32%

dichloromethane (75-09-2) + dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + silver trifluoromethanesulfonate (2923-28-6) + acetonitrile (75-05-8) → (1,1'-bis(diisopropylphosphino)ferrocene)Pd(acetonitrile)(water) trifluoromethanesulfonate*2(dichloromethane)*2(water)

Conditions	Yield
In dichloromethane; acetonitrile byproducts: AgCl; N2; add. of acetonitrile soln. of silver salt to dichloromethane soln. of Pd complex, stirring for 5 min at room temp.; filtration, evapn. at room temp., recrystn. from CH2Cl2; elem. anal.;	60%

dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + sodium iodide (7681-82-5) → [Pd(dippf)I2]

Conditions	Yield
In acetone for 22h; Inert atmosphere; Schlenk technique;	48%

dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II) (215788-65-1) + water (7732-18-5) + silver(I) 4-methylbenzenesulfonate (16836-95-6) → [Pd(H2O)(1,1'-bis(diisopropylphosphino)ferrocene)(tosylato)](tosylate) (849062-58-4)

Conditions	Yield
In dichloromethane (N2); using Schlenk techniques; addn. of AgO3SC6H4CH3 to soln. of PdCl2(Fe(C5H4P(i-Pr)2)2) in CH2Cl2 at room temp.; stirring at room temp. for 2h; filtration, concn., addn. of Et2O, pptn., filtration, washing with Et2O,drying under N2; elem. anal.;

Upstream product

• 97239-80-0 1,1'-bis(diisopropylphosphino)ferrocene 

Downstream Products

• 403609-50-7 [1,1'-bis(diisopropylphosphino)ferrocene]palladium(II) 3,6-dichloro-1,2-benzenedithiolate 
• 849062-58-4 [Pd(H₂O)(1,1'-bis(diisopropylphosphino)ferrocene)(tosylato)](tosylate) 

Relevant articles and documents

Bidentate ferrocenylphosphines and their palladium(II)dichloride complexes - X-ray structural and NMR spectroscopic investigations and first results of their characteristics in the Pd-catalysed cooligomerisation of 1,3-butadiene with CO2

The chiral 1,1′-bis(di(+)-menthylphosphino)ferrocene (dmenpf, 1b) and achiral 1,1′-bis(diisopropylphosphino)ferrocene (disoppf, 1a) were prepared from the corresponding tertiary chlorophosphines 2b and 2a and the dilithiated ferrocene-TMEDA complex as analytically pure crystals. The synclinic eclipsed conformation of the Cp rings and the Cp(1)-Fe-Cp(1)′ angle in 1b was determined to be 175.0(2)° by X-ray structure analysis. With H2[PdCl4] 1a forms the bimetallic complex (disoppf)PdCl2 (3a). In contrast to the structure of the free ligand disoppf (1a), the X-ray structure of 3a and the NMR spectra in solution as well as in the solid state show that the P atoms are chemically and magnetically equivalent. The conformation of the Cp rings converts from an eclipsed to a staggered conformation. The ferrocene-based ligands show significant activity in the Pd-catalysed cooligomerisation of 1,3-butadiene with CO2