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804959 Sigma-Aldrich

DavePhos-Pd-G3

95%

Synonym: Methanesulfonato 2-dicyclohexylphosphino-2-(N,N-dimethylamino)biphenyl(2′-amino-1,1′-biphenyl-2-yl) palladium(II)

  • CAS Number 1445085-87-9

  • Empirical Formula (Hill Notation) C39H49N2O3PPdS

  • Molecular Weight 763.28

  •  MDL number MFCD27978422

  •  PubChem Substance ID 329768911

  •  NACRES NA.22

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Properties

Related Categories Buchwald Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, Homogeneous Pd Catalysts, Palladium Catalysts,
Quality Level   100
assay   95%
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reaction type: Heck Reaction
  reaction type: Hiyama Coupling
  reaction type: Negishi Coupling
  reaction type: Sonogashira Coupling
  reaction type: Stille Coupling
  reaction type: Suzuki-Miyaura Coupling
  reagent type: catalyst
reaction type: Cross Couplings
  reagent type: ligand
impurities   <5% THF
mp   183-200 °C (decomp)
functional group   phosphine
SMILES string   CN(C)C1=C(C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2)C=CC=C1.NC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5
InChI   1S/C26H36NP.C12H10N.CH4O3S.Pd/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h9-12,17-22H,3-8,13-16H2,1-2H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1
InChI key   FBIRGVXUSGLNQE-UHFFFAOYSA-M

Description

General description

DavePhos-Pd-G3 is a modified G3 precatalyst (G3′). It has been synthesized by Buchwald and coworkers from second generation (G2) precatalyst by methylation of the amino group present on biphenyl backbone. It is a useful catalyst for various cross-coupling reactions. They are versatile catalysts. They have long life in solutions and are readily soluble in various organic solvents. G3- precatalysts have been employed in various C-N bond forming reactions.

Application

Pd precatalyst for cross-coupling

Packaging

1, 5 g in glass bottle

250 mg in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

G3 and G4 Buchwald Precatalysts

Visit Stephen Buchwald’s Professor Product Portal for more information on palladium precatalysts and products offered by the Buchwald Laboratory.
Keywords: Aminations, Arylations, Catalysis, Coupling reactions, Cross couplings, Deprotonations, Hydroxylations, Ligands, Pharmaceutical, Solvents, Suzuki-Miyaura coupling

KitAlysis™ C-N (Buchwald-Hartwig) High-Throughput Screening Kit

The screening sets come pre-loaded with 1 µmol of catalyst in each vial according to the following design.
Keywords: Cross couplings, High performance liquid chromatography, Ligands, Solvents

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive t...
Keywords: Coupling reactions, Cross couplings, Solvents

Stephen Buchwald Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Stephen Buchwald Group – Professor Product Portal
Keywords: Aminations, Asymmetric catalysis, Asymmetric synthesis, Catalysis, Coupling reactions, Cross couplings, Fluorinations, Ligands, Solvents, transformation

Related Content

KitAlysis™ High-Throughput Screening Kits: A Visual Introductory Guide [VIDEO]

This KitAlysis™ High-Throughput Screening Kits video animation clearly illustrates the step by step process that enables any chemist to quickly and efficiently screen 24 unique cross-coupling reactio...
Keywords: Coupling reactions, Cross couplings

Peer-Reviewed Papers
15

References

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