CAS 12150-46-8 1,1'-Bis(diphenylphosphino)ferrocene

Synonyms

1,1'-Ferrocenediyl-bis(diphenylphosphine); DPPF

IUPAC Name

1,1-Bis(diphenylphosphino)ferrocene

Molecular Weight

554.38

Molecular Formula

C34H28FeP2

Boiling Point

363.8ºC at 760mmHg

Melting Point

181-182 °C(dec.)(lit.)

Flash Point

182.8ºC

Purity

98%

Appearance

Solid

Storage

2-8°C

Exact Mass

554.10200

Stability

Stable. Incompatible with strong oxidizing agents.

Application

1,1'-Bis(diphenylphosphino)ferrocene serves as a versatile ligand in the synthesis of coordination compounds and plays a crucial role in forming complexes with various metals. Renowned for its deep yellow crystalline powder form, this compound is indispensable in palladium-catalyzed coupling reactions, such as the formation of (dppf)PdCl2 when reacting with acetonitrile or benzonitrile complexes of PdCl2. It acts as an effective ligand in homogeneous catalysis, facilitating ruthenium-catalyzed greener amine synthesis through hydrogen-borrowing, and is essential in Buchwald-Hartwig cross-coupling. Additionally, it supports numerous catalytic processes, including Pd-catalyzed cross-coupling, carbon-nitrogen, and carbon-oxygen bond formation, Ni-catalyzed amination of aryl chlorides, and conversion of aryl halides to aryl nitriles. It also plays a role in Ni-catalyzed Suzuki reactions, hydroamination of 1,3-dienes, and regioselective Pd-catalyzed hydrophosphinylation, which forms branched alkenes. Furthermore, it acts as a ligand for Ru-catalyzed reduction of nitriles to primary amines, Rh-catalyzed processes such as alkyne head-to-tail dimerization, and olefin isomerization, as well as Ni or Rh-catalyzed borylation, underpinning its vital function in synthesizing novel functionalized furan derivatives through Pd-phosphine sequential C-C and C-O bond formation.

December 09, 2024

Versatile Ligand for Catalysis and Synthesis

I've used Alfa Chemistry's 1,1'-Bis(diphenylphosphino)ferrocene in palladium-catalyzed coupling reactions with great success. The deep yellow powder facilitated efficient Suzuki and Buchwald-Hartwig cross-couplings, enhancing my research productivity significantly.