EMAIL THIS PAGE TO A FRIEND
638021 Sigma-Aldrich

DavePhos

97%

Synonym: 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl

  • CAS Number 213697-53-1

  • Empirical Formula (Hill Notation) C26H36NP

  • Molecular Weight 393.54

  •  MDL number MFCD02183572

  •  PubChem Substance ID 24882905

  •  NACRES NA.22

Purchase

Properties

Related Categories Buchwald Ligands, Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis,
InChI Key   ZEMZPXWZVTUONV-UHFFFAOYSA-N
Quality Level   200
assay   97%
mp   121-124 °C (lit.)
functional group   phosphine
reaction suitability   reaction type: Cross Couplings
  reagent type: ligand
reaction type: Arylations
  reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reagent type: ligand
reaction type: Hydroaminations
  reagent type: ligand
reaction type: Kumada Coupling
  reagent type: ligand
reaction type: Negishi Coupling
  reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Description

Application

DavePhos may be used as a ligand in the following reactions:
• Palladium catalyzed sp3 arylation of 2-substituted-N-iminopyridinium ylides with different aryl chlorides to yield functionalized pyridines.
• Preparation of functionalized benzylic sulfones via palladium-catalyzed Negishi cross-coupling between alkyl sulfones and aryl halides.
• C-C Coupling of 3-haloquinolines with aryl sulfinates via palladium-catalyzed desulfitative arylation to form the corresponding biaryl compounds.

Ligand used in a Pd-catalyzed Suzuki aryl-aryl coupling leading to benzodioxepines.

Useful ligand for Pd-catalyzed C-N bond formation; amination of aryl halides containing hydroxyl, amide, or enolizable ketones.

Packaging

1, 5, 25, 100 g in glass bottle

Legal Information

Usage subject to US Patents 6307087 and 6395916.

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

Buchwald Phosphine Ligands - Technical Article

Over the past several years, the Buchwald group has developed a series of bulky electron-rich phosphines that have garnered much attention for their ability to effect various C–C, C–N, and C–O bond f...
Keywords: Aldrichimica Acta, Arylations, C-X bond formation, Catalysis, Chemfiles, Coupling reactions, Ligands, Methods, Type

Buchwald Phosphine Ligands

Sigma-Aldrich is pleased to offer an array of phosphines for C-C, C-N, and C-O bond formation.
ChemFiles Volume 4 Article 2
Keywords: Amidations, Aminations, Applications, Arylations, Catalysis, Coupling reactions, Cross couplings, Ligands, Organic synthesis, Sonogashira Coupling, Suzuki-Miyaura coupling

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

Buchwald Phosphine Ligands - For C-C, C-N, and C-O Bond Formation

For C-C, C-N, and C-O Bond Formation: Over the past several years, the Buchwald group has developed a series of bulky electron-rich phosphines that have garnered much attention for their ability to e...
Keywords: Aldrichimica Acta, Arylations, Catalysis, Chemfiles, Coupling reactions, Ligands, Methods, Type

Buchwald Precatalysts and Ligand Guide

Dialkylbiaryl phospine ligands, and the precatalysts derived from them, are commonly referred to as Buchwald Precatalysts and Ligands. These reagents have developed into a highly valuable class of co...
Keywords: Catalysis, Ligands

Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?