32660-24-5

Basic information

• Product Name: bis(2-(diphenylphosphoryl)cyclopenta-2,4-dien-1-yl)iron
• Synonyms: bis(2-(diphenylphosphoryl)cyclopenta-2,4-dien-1-yl)iron
• CAS NO: 32660-24-5
• Molecular Weight: 586.39
• Mol File: 32660-24-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: bis(2-(diphenylphosphoryl)cyclopenta-2,4-dien-1-yl)iron(CAS DataBase Reference)
• NIST Chemistry Reference: bis(2-(diphenylphosphoryl)cyclopenta-2,4-dien-1-yl)iron(32660-24-5)
• EPA Substance Registry System: bis(2-(diphenylphosphoryl)cyclopenta-2,4-dien-1-yl)iron(32660-24-5)

Safety Data

• Hazardous Substances Data: 32660-24-5(Hazardous Substances Data)

Upstream product

• 12150-46-8 1,1'-bis-(diphenylphosphino)ferrocene 
• 7722-84-1 dihydrogen peroxide 
• 7732-18-5 water 
• 1310-73-2 sodium hydroxide 
• 1072-71-5 2,5-Dimercapto-1,3,4-thiadiazole 
• 98-83-9 isopropenylbenzene 
• 103-84-4 Acetanilid 
• 3375-31-3 palladium diacetate 

Downstream Products

• 12150-46-8 1,1'-bis-(diphenylphosphino)ferrocene 
• 1338578-73-6 [CoCl₂(1,1'-bis(diphenylphosphino)ferrocene dioxide-O,O')] 
• 511243-10-0 [CoI₂(1,1'-bis(diphenylphosphino)ferrocene dioxide-O,O')] 
• 1338578-74-7 [CoBr₂(1,1'-bis(diphenylphosphino)ferrocene dioxide-O,O')] 

Relevant articles and documents

Air-stable phosphine organocatalysts for the hydroarsination reaction

Readily-available triarylphosphines are explored as organocatalysts for the hydroarsination reaction. When compared to transition metal catalysis, phosphine organocatalysis greatly improved solvent compatibility of the hydroarsination of nitrostyrenes. Upon complete conversion, arsine products were isolated in up to 99% yield while up to 48% of the phosphine catalyst was still active. A mechanism was proposed and structure-activity analysis regarding catalyst activity concluded that sterically-bulkier catalysts were effective at minimizing catalyst deactivation.

Role of dppf Monoxide in the Transmetalation Step of the Suzuki-Miyaura Coupling Reaction

Diphosphine ligands are frequently used in palladium-catalyzed Suzuki-Miyaura (S-M) reactions. Despite their widespread application in both academic and industrial settings, their role in the B-to-Pd transmetalation has not been firmly established. We combined electrochemistry, NMR spectroscopy, and DFT calculations to elucidate the role of dppf (1,1′-bis(diphenylphosphino)ferrocene) in this key elementary step of the S-M reaction. We observed that excess dppf inhibits transmetalation involving PhB(OH)2 and dppf-ligated arylpalladium(II) complexes, while an optimal [base]/[PhB(OH)2] ratio maximizes the concentration of a [Pd-O-B] key intermediate. In situ oxidation of dppf to the diphosphine monoxide dppfO can take place in the presence of base, leading to dppfO-ligated arylpalladium(II) complexes, which readily undergo transmetalation at room temperature. These findings suggest guidelines for the rational optimization of diphosphine-promoted S-M reactions.

Radical C-H Arylation of Oxazoles with Aryl Iodides: Dppf as an Electron-Transfer Mediator for Cs2CO3

A radical C-H arylation reaction of oxazoles with (hetero)aryl iodides using Cs2CO3 as base/electron donor and 1,1′-bis(diphenylphosphino) ferrocene (dppf) as a catalytic SET mediator is reported. The overall reaction likely follows the general base-promoted homolytic aromatic substitution mechanism through a radical-chain pathway. DFT calculations suggest that dppf forms a complex with CsCO3-, enhancing its SET reducing ability to generate an aryl radical from ArI.