1,1'-Bis(diphenylphosphino)ferrocene

Description

1,1'-Bis(diphenylphosphino)ferrocene (Dppf) is a diphosphine ligand used in homogeneous catalysis. Dppf is commonly used in palladium-catalyzed coupling reactions, but also is used with a variety of other Group 9 and 10 transition metals such as rhodium and nickel.

Chemical properties

1,1'-Bis(diphenylphosphino)ferrocene is deep yellow crystalline powder

The Uses of 1,1'-Bis(diphenylphosphino)ferrocene

1,1'-Bis(diphenylphosphino)ferrocene acts as a ligand in homogeneous catalysis. It is used as a ligand for ruthenium-catalyzed greener amine synthesis from amines and alcohols by hydrogen-borrowing. It is also employed as a ligand for Buchwald-Hartwig cross coupling. Further, it is used in the synthesis of coordination compound as well as the formation of complexes with various metals such as palladium chloride. In addition to this, it serves as a reagent for palladium-catalyzed coupling reactions and also plays an important role in Suzuki reaction.

The Uses of 1,1'-Bis(diphenylphosphino)ferrocene

To a solution of the SM (16.53 g, 72 mmol) in DMF (20 mL) was added dppf (8 g, 14.43 mmol) and ZnCN2 (5.08 g, 43.3 mmol), followed by Pd2(dba)3 (6.61 g, 7.22 mmol). The mixture was stirred at reflux for 16 h, cooled to RT, and concentrated in vacuo. EtOAc (1.0 L) was added to the crude and the resulting suspension was filtered. The filtrate was washed with H2O (1.0 L) and the aq layer extracted with EtOAc (2 x 1.0 L). The combined org extracts were washed with brine (1.0 L), dried (MgSO4), and concentrated in vacuo. The resulting material was purified by column chromatography (eluting with 5% EtOAc/pentane) to provide the product as a solid. [13.7 g, 88%]

The Uses of 1,1'-Bis(diphenylphosphino)ferrocene

1,1'-Bis(diphenylphosphino)ferrocene used coordination compound in synthesis, readily forms complexes with various metals, i.e. when reacting with the acetonitrile or benzonitrile complexes of PdCl2 it forms (dppf)PdCl2, which i s a popular reagent for palladium-catalyzed coupling reactions.

General Description

Novel functionalized furan derivatives were prepared via Pd-phosphine sequential C-C and C-O bond formation.

Purification Methods

Wash it with distilled H2O and dry it in a vacuum. Dissolve it in ca 5 parts of hot dioxane and cool to give orange crystals m 181-183o. Recrystallisation from *C6H6/heptane (1:2) gives a product with m 183-184o. [Bishop et al. J Organomet Chem 27 241 1971.]