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675784

Sigma-Aldrich

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

Synonym(s):

QPhos

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About This Item

Linear Formula:
[(C6H5)5C5]Fe[C5H4(P(C4H9)2)]
CAS Number:
312959-24-3
Molecular Weight:
710.71
MDL number:
MFCD03788940
UNSPSC Code:
12352005
PubChem Substance ID:
24885299
NACRES:
NA.22

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

mp

211-219 °C

functional group

phosphine

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Takuo Hama et al.
Journal of the American Chemical Society, 128(15), 4976-4985 (2006-04-13)
The intermolecular alpha-arylation and vinylation of amides by palladium-catalyzed coupling of aryl bromides and vinyl bromides with zinc enolates of amides is reported. Reactions of three different types of zinc enolates have been developed. The reactions of aryl halides occur

Articles

Q-Phos

Developed by Professor John Hartwig, pentaphenyl(di-tert-butylphosphino)ferrocene (Q-Phos) has emerged to be a premier ligand in coupling reactions with its remarkably broad utility in a variety of C–N, C–O, and C–C bondforming reactions.

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