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675784 Sigma-Aldrich

1,2,3,4,5-Pentaphenyl-1′-(di-tert-butylphosphino)ferrocene

Synonym: QPhos

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Phosphine Compounds, Phosphine Ligands, Q-Phos More...
mp   211-219 °C
functional group   phosphine
reaction suitability   reagent type: ligand
reaction type: Arylations
  reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reagent type: ligand
reaction type: Sonogashira Coupling
  reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
SMILES string   [Fe].CC(C)(C)P([C]1[CH][CH][CH][CH]1)C(C)(C)C.c2ccc(cc2)[C]3[C]([C]([C]([C]3c4ccccc4)c5ccccc5)c6ccccc6)c7ccccc7
InChI   1S/C35H25.C13H22P.Fe/c1-6-16-26(17-7-1)31-32(27-18-8-2-9-19-27)34(29-22-12-4-13-23-29)35(30-24-14-5-15-25-30)33(31)28-20-10-3-11-21-28;1-12(2,3)14(13(4,5)6)11-9-7-8-10-11;/h1-25H;7-10H,1-6H3;
InChI key   YOQRDWPCPFCDLP-UHFFFAOYSA-N

Description

Packaging

100, 500 mg in glass bottle

Application

Sterically hindered phosphine with broad application in a variety of palladium-catalyzed amination and etherification reactions of aryl chlorides.

Legal Information

Sold in collaboration with Johnson Matthey Catalyst for research purposes only. US6562989 B2 and any patents arising therefrom apply.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Hartwig Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Hartwig Group – Professor Product Portal
Keywords: Aminations, Asymmetric synthesis, Catalysis, Cross couplings, Fluorinations, Hydroaminations, Infrared spectroscopy, Ligands, Oxidations, Silylations, Suzuki reactions

Heteroatom Formylation

Formate esters and formamides are valuable synthetic intermediates, and a variety of synthetic protocols have been devised for formylation of heteroatoms including the use of in situ-generated formic...
Aldrich ChemFiles 2007, 7.1, 9.
Keywords: Condensations, Formylation reaction, Formylations, Protocols, Solvents

Q-Phos - Technical Article

The use of electron-rich, sterically congested monodentate phosphine ligands, in conjunction with a metal complex, has become a common paradigm in transition metal catalyzed coupling reactions. Devel...
William Sommer
ChemFiles 2007, 7.10, 12.
Keywords: Alkylations, Aminations, Arylations, Catalysis, Coupling reactions, Decarboxylations, Etherifications, Ligands, Transmetalation

Suzuki-Miyaura Coupling and a-Arylation

Suzuki-Miyaura coupling reactions using a Pd catalyst derived from Q-Phos are highly successful for both electron-poor and electron-rich aryl bromides and chlorides (Table 3).1 As expected, aryl brom...
Aldrich ChemFiles 2007, 7.5, 11.
Keywords: Alkylations, Arylations, Catalysis, Coupling reactions, Cross couplings, Decarboxylations, Ligands, Suzuki-Miyaura coupling, Transmetalation

Peer-Reviewed Papers
15

References

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