675784

Sigma-Aldrich

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

Synonym(s):
QPhos
Linear Formula:
(C6H5)5C5FeC5H4(P(C4H9)2)
CAS Number:
Molecular Weight:
710.71
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

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

Quality Level

mp

211-219 °C

functional group

phosphine

SMILES string

Fe.CC(C)(C)P(C1CHCHCHCH1)C(C)(C)C.c2ccc(cc2)C3C(C(C(C3c4ccccc4)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

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

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
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.
Read More
Related Content
Professor Hartwig's research focuses on the discovery and understanding of new reactions catalyzed by transition metal complexes.
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