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763381 Sigma-Aldrich

XPhos Pd G3

95%

Synonym: (2-Dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate, XPhos-G3-Palladacycle, XPhos-Pd-G3

  • CAS Number 1445085-55-1

  • Empirical Formula (Hill Notation) C46H62NO3PPdS

  • Molecular Weight 846.45

  •  MDL number MFCD22666043

  •  PubChem Substance ID 329767048

  •  NACRES NA.22

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Properties

Related Categories Buchwald 3rd Generation Palladacycles, Buchwald Ligands and Complexes, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling,
Quality Level   100
assay   95%
mp   146-151 °C (decomposition)
functional group   phosphine
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
SMILES string   CC(C)C(C=C1C(C)C)=CC(C(C)C)=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.NC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5
InChI   1S/C33H49P.C12H10N.CH4O3S.Pd/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1
InChI key   NKKHABPORDUWIG-UHFFFAOYSA-M

Description

General description

XPhos Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. XPhos Pd G3 is an excellent reagent for Suzuki cross-coupling reactions. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

XPhos Pd G3 may be used in the following reactions:
• Cyanation reaction of heterocyclic halides.
• Coupling of heteroaryl chlorides with polyfluoroaryl zinc reagents.
• Coupling of 2,6-difluorophenylboronic acid with (hetero)aryl chlorides.

Packaging

1, 5 g in glass bottle

250 mg in glass bottle

Safety & Documentation

Safety Information

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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Certificate of Origin (COO)

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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 High-Throughput Palladium Precatalyst Cross-Coupling Reaction Screening Kit

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

KitAlysis Suzuki-Miyaura Cross-Coupling 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

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

Suzuki-Miyaura Cross-Coupling 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

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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