1,1μ-Bis(di-cyclohexylphosphino)ferrocene palladium dichloride

Uses

1,1'-Bis(di-cyclohexylphosphino)ferrocene palladium dichloride is an air-stable catalyst useful in the arylation of various ketones with aryl chlorides and aryl bromides.

Uses

1,1′-Bis(di-cyclohexylphosphino)ferrocene]dichloropalladium(II) or (Pd(dcpf)Cl₂) can be used as a catalyst in the synthesis of:

• α, β-unsaturated amides by hydroaminocarbonylation of alkynes with tertiary amines.
• Quinazoline derivatives via Suzuki-Miyaura coupling reaction between of quinazolines containing unprotected NH₂ group and arylboronic acids.
• α-aryl carbonyl compounds by α-arylation of ketones with aryl chlorides and aryl bromides.

reaction suitability

core: palladium
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

The thimble of a 250 mL Soxhlet apparatus was charged with 10 g of anhydrous NiBr2. The air in the apparatus was replaced with nitrogen, and 150 mL of ethylene glycol dimethyl ether was added to the flask with a condenser attached. The solid was heated to reflux and extracted for 1 week under nitrogen protection. Occasionally, solid pieces of NiBr2 were broken up with a spatula. Excess solvent was removed by vacuum distillation and the resulting orange-colored solid was dried under vacuum overnight. Nickel dibromide and dimethoxyethane (8.5 g, 63%) was stored in a glove box filled with nitrogen. Higher yields were obtained by extending the extraction time, as some NiBr2 remained in the thimble after one week.