403815-19-0

Basic information

• Product Name: 1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene
• Synonyms: 1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene
• CAS NO: 403815-19-0
• Molecular Weight: 1034.96
• Mol File: 403815-19-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene(403815-19-0)
• EPA Substance Registry System: 1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene(403815-19-0)

Safety Data

• Hazardous Substances Data: 403815-19-0(Hazardous Substances Data)

Usage

Reaction

Ligand/palladium complex used in the direct arylation of heteroaromatic compounds with congested, functionalized aryl bromides. Suzuki-Miyaura Coupling of Aryl Bromides and Chlorides bearing alkyl, methoxy, keto, nitrile, etc. substitution to phenyl- and methoxybenzene boronic acids at Low Palladium Loading. Heck Coupling of Functionalized Aryl Bromides to n-butyl acrylate, styrene and n-butyl vinyl ether at Low Palladium Loading. Additional catalyzed reaction include Allylic Amination of Monoterpene Derivatives including geranylacetate, nerylacetate, linalylacetate and perillylacetate at Low Palladium Loading, and Sonogashira Cross-Coupling of Aryl Bromides by using stabilizing new copper-tetraphosphane adducts.

Upstream product

• 878190-70-6 [(bis(5-methyl-2-furyl)phosphino)cyclopentadienyl]lithium 
• 83272-80-4 lithium diphenylphosphinocyclopentadienyl 

Downstream Products

• 460049-14-3 Fe((CH₃)3CC₅H₂(P(C₆H₅)2)2)2Mo(CO)3 
• 403815-24-7 Fe(C₅H₂C(CH₃)3(P(C₆H₅)2)2)2RhClCO 
• 403815-25-8 Fe(C₅H₂C(CH₃)3(P(C₆H₅)2)2)2Rh(CO)2⁽¹⁺⁾*RhCl₂(CO)2^(1-)=Fe(C₅H₂C(CH₃)3(P(C₆H₅)2)2)2Rh(CO)2RhCl₂(CO)2 
• 403815-23-6 Fe(C₅H₂C(CH₃)3(P(C₆H₅)2)2)2Rh(CO)2⁽¹⁺⁾*BF₄^(1-)=Fe(C₅H₂C(CH₃)3(P(C₆H₅)2)2)2Rh(CO)2BF₄ 
• 460049-12-1 Fe((CH₃)3CC₅H₂(P(C₆H₅)2)2)2Cr(CO)3 
• 623946-94-1 Fe(C₅H₂C(CH₃)3(P(C₆H₅)2)2)2PdCl₂ 
• 623946-94-1 [PdCl₂(1,1',2,2'-tetrakis(diphenylphosphino)-4,4'-di-tert-butylferrocene)] 
• 1011480-81-1 [PdBr₂(1,1'2,2'-tetrakis(diphenylphosphino)-4,4'-di-tert-butylferrocene)] 
• 67675-73-4 catena[(μ3-iodo)(acetonitrile-N)copper(I)] 
• 1016567-35-3 P,P',P''-[1,1',2,2'-tetrakis(diphenylphosphino)-4,4'-di-tert-butylferrocene]iodocopper(I) 
• 1016567-40-0 P,P',P''-[1,1',2,3'-tetrakis(diphenylphosphino)-4,4'-di-tert-butylferrocene]iodocopper(I) 

Relevant articles and documents

A sterically congested 1,2-diphosphino-1′-boryl-ferrocene: Synthesis, characterization and coordination to platinum

A new class of tritopic ferrocene-based ambiphilic compounds has been prepared by assembling diphosphino- and boryl-substituted cyclopentadienides at iron. The presence of five sterically demanding substituents on the ferrocene platform induces conformational constraints, as is apparent from XRD and NMR data, but does not prevent the chelating coordination to platinum. The Lewis acid moiety is pendant in both the free ligand and the platinum complex.

Conformational control of metallocene backbone by cyclopentadienyl ring substitution: A new concept in polyphosphane ligands evidenced by "through-space" nuclear spin-spin coupling. Application in heteroaromatics arylation by direct C-H activation

The present study deals with the conformational control of the metallocene backbone within ferrocenyl polyphosphane ligands and their performance in the highly topical palladium-catalyzed heteroaromatics arylation by direct C-H activation. New substituted

First copper(I) ferrocenyltetraphosphine complexes: Possible involvement in Sonogashira cross-coupling reaction?

Preparation and characterization of the first examples of copper(I) ferrocenylpolyphosphine complexes are reported. The molecular structure of complex {P,P′,P″-[1,1′,2,2′-tetrakis(diphenylphosphino)- 4,4′-di-tert-butylferrocene]iodocopper(I)} (1) was solved by X-ray diffraction studies, and its fluxional behavior in solution was investigated by VT-31P NMR; both revealed a net triligated coordination preference of the ferrocenyl tetraphosphine Fc(P)4tBu with copper. The tetradentate ligand is an active auxiliary in Sonogashira alkynylation; therefore the general question of copper as a competitive coordination partner in the Pd/Cu-catalyzed Sonogashira reaction was raised and discussed. Electronically neutral, activated, and deactivated aryl bromides were employed for coupling with phenylacetylene with various [(Pd)/(Cu)/(tetraphosphine)] systems. The catalytic investigations shown that 1 mol % of complex 1 in combination with palladium is far more effective and selective for Sonogashira coupling than 5 mol % of CuI and palladium in the coupling to phenylacetylene of the deactivated aryl bromide 4-bromoanisole. This system efficiently avoids the concurrent and deleterious consumption of phenylacetylene by formation of diyne or enynes. To our knowledge, this is the first time that this kind of high selectivity is induced in Sonogashira alkynylation by initial ligand complexation to copper instead of palladium. These results demonstrate that coordination of Cu halide cocatalyst is a factor that should no longer be neglected in mechanistic and applied studies of the Sonogashira reaction.