XPhos Pd G4 Chemical Properties

Melting point:

150 °C

storage temp. 

2-8°C, protect from light, stored under nitrogen

form 

Powder

color 

white to off-white

InChI

InChI=1S/C33H49P.C13H11N.CH4O3S.Pd/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3;2-7,9-10H,1H3;1H3,(H,2,3,4);/q;-2;;+2

InChIKey

RWNNUNWRORBXQJ-UHFFFAOYSA-N

SMILES

P(C1CCCCC1)(C1CCCCC1)(C1C=CC=CC=1C1C(=CC(C(C)C)=CC=1C(C)C)C(C)C)[Pd+2]1(N(C2=CC=CC=C2C2=CC=CC=[C-]12)C)[O-]S(=O)(=O)C

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

XPhos Pd G4 Usage And Synthesis

Chemical Properties

Powder. Bench stable, soluble in most organic solvents.

Uses

XPhos Pd G4 is a powerful ligand for classic cross-coupling reactions combined with the Buchwald Fourth Generation Palladacycle.

Reactions

Palladium catalyst used in the Suzuki-Miyaura coupling of unstable boronic acids.

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst

Synthesis

A dry round-bottomed flask (25 mL) was equipped with a stirring bar and then palladium dimer methanesulfonate (1 mmol) and XPhos (0.953 g) were added to the reaction flask under nitrogen atmosphere. Dry dichloromethane was added to the above reaction mixture as reaction solvent (10 mL) and the mixture was stirred at room temperature for 16 hours. At the end of the reaction the resulting reaction mixture was concentrated under vacuum making the total volume of the mixture about 1-2 mL. To the above reaction mixture n-pentane (20 mL) was added to precipitate a black solid and the mixture was filtered. The resulting filtrate was concentrated in vacuo to afford XPhos Pd G4, (SP-4-3)-[dicyclohexyl[2',4',6'-tris(isopropyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonic acid)[2'-(methylamino)[1,1'-biphenyl]-2-yl]palladium.

XPhos Pd G4(1599466-81-5)Related Product Information

• Methanesulfonato(triphenylphosphine)(2'-amino-1,1'-biphenyl-2-yl)palladium(II) (PPH3 PD G3)
• XPhos Pd G3
• SPhos Palladacycle Gen. 4
• Xantphos Pd G3
• BrettPhos Pd G3
• XPhos Pd G2
• RuPhos Pd G1 Methyl t--Butyl Ether Adduct
• SPhos Pd G2
• BrettPhosPalladacycle
• Palladacycle Gen. 3
• t-BuXphos Palladacycle Gen. 4
• RuPhos Palladacycle Gen. 4
• t-BuBrettPhos Palladacycle Gen. 3
• SPhos Pd G3
• SPhos Pd G1, Methyl t-Butyl Ether Adduct
• RuPhos Pd G2
• tBuXPhos Pd G1
• XPhos Pd G1