180690-22-6

Basic information

• Product Name: [Fe(C₅H₄)2(P(C₆H₅)2)2]Pd(C₆H₅)(N(CH₃C₆H₄)2)
• Synonyms: [Fe(C₅H₄)2(P(C₆H₅)2)2]Pd(C₆H₅)(N(CH₃C₆H₄)2)
• CAS NO: 180690-22-6
• Molecular Weight: 934.188
• Mol File: 180690-22-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [Fe(C₅H₄)2(P(C₆H₅)2)2]Pd(C₆H₅)(N(CH₃C₆H₄)2)(CAS DataBase Reference)
• NIST Chemistry Reference: [Fe(C₅H₄)2(P(C₆H₅)2)2]Pd(C₆H₅)(N(CH₃C₆H₄)2)(180690-22-6)
• EPA Substance Registry System: [Fe(C₅H₄)2(P(C₆H₅)2)2]Pd(C₆H₅)(N(CH₃C₆H₄)2)(180690-22-6)

Safety Data

• Hazardous Substances Data: 180690-22-6(Hazardous Substances Data)

Upstream product

• 12150-46-8 1,1'-bis-(diphenylphosphino)ferrocene 
• 180690-23-7 Pd(P(C₆H₅)3)2(C₆H₅)(N(C₆H₄CH₃)2) 

Downstream Products

• 14221-01-3 tetrakis(triphenylphosphine) palladium⁽⁰⁾ 

Relevant articles and documents

Carbon-nitrogen-bond-forming reductive elimination of arylamines from palladium(II) phosphine complexes

A series of monomeric palladium amido complexes of the form trans-(PPh3)2Pd(Ar)(NAr'2) and (DPPF)Pd(Ar)NAr'2) (DPPF = 1,1'-bis(diphenylphosphino)ferrocene) and dimeric palladium amido complexes of the form {(PPH3)Pd(Ar)μ-NHR)}2 (R = Ph, t-Bu) have been prepared by the reaction of lithium and potassium amides with palladium aryl halide complexes. An X-ray crystal structure of (DPPF)Pd(p-NMe2C6H4)[N(p-CH3C6H4)2] was obtained. Upon thermolysis in the presence of PPh3, serving as a trapping agent, both the monomeric and dimeric palladium amido complexes underwent C-N-bond-forming reductive elimination to form arylamines in high yields along with a Pd(0) species. Reductive elimination was also observed from azametallacycle (PPh3)Pd(η2-C6H4C6H4-NH), to form carbazole and Pd(PPh3)4 at room temperature. Mechanistic studies on the reductive elimination reactions of the monomeric PPh3-ligated amido complexes indicated the presence of two competing pathways for the formation of amine. At low [PPh3], reductive elimination occurs via phosphine dissociation to form a three-coordinate intermediate; however, as [PPh3] is increased, a pathway of reductive elimination from a four-coordinate complex becomes dominant. The DPPF-ligated palladium amido complexes directly eliminated amine from the four-coordinate complex. The mechanism of the reductive elimination from dimeric palladium amido complexes was also studied. These complexes undergo reductive elimination of amine via dimer dissociation to generate a three-coordinate intermediate analogous to those formed by the PPh3-ligated monomeric amido complexes. The C-N-bond forming reductive elimination reactions were accelerated by electron-withdrawing groups on the Pd bound aryl group and by electron-donating groups on the amido ligand, suggesting that the aryl group acts as an electrophile and the amido ligand acts as a nucleophile.