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675709 Sigma-Aldrich

2′-(Dicyclohexylphosphino)acetophenone ethylene ketal

97%

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Phosphine Compounds, Phosphine Ligands, Symphos More...
assay   97%
mp   85-92 °C
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: ligand
SMILES string   CC1(OCCO1)c2ccccc2P(C3CCCCC3)C4CCCCC4
InChI   1S/C22H33O2P/c1-22(23-16-17-24-22)20-14-8-9-15-21(20)25(18-10-4-2-5-11-18)19-12-6-3-7-13-19/h8-9,14-15,18-19H,2-7,10-13,16-17H2,1H3
InChI key   ZQASITYRQOCACA-UHFFFAOYSA-N

Description

Application

Cocatalyst for:
• Palladium-catalyzed amination reactions
• Palladium/P,O-Ligand-catalyzed Suzuki cross-coupling

A P-O ligand that in combination with Pd2(dba)3 (cat. no. 328774) provides an active catalyst that effectively cross-couples a variety of arylboronic acids with aryl chlorides containing either electron-rich or electron-poor substituents.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Chiral Phosphoric Acids

BINOL-derived phosphoric acids are capable of catalyzing a range of interesting processes of which nucleophilic addition reactions to imine substrates are particularly noteworthy. List and coworkers ...
Aldrich ChemFiles 2007, 7.9, 11.
Keywords: Addition reactions, Aminations, Asymmetric synthesis, Catalysis, Chemfiles, Diels-Alder reaction, Nucleophilic additions, Pictet-Spengler reaction, Reductions, Reductive aminations

Symphos

A new class of phenyl-backbone derived P,O-ligands (Symphos) were developed by Symyx Technologies in collaboration with professor Fu and coworkers.1 These new ligands proved to be suitable for genera...
William Sommer
Aldrich ChemFiles 2007, 7.10, 11.
Keywords: Catalysis, Chemfiles, Cross couplings, Ligands

Related Content

Symphos Ligands for Efficient Suzuki Cross Coupling

A new class of phenyl-backbone derived P,O-ligands (Symphos) were developed by Symyx Technologies in collaboration with professor Fu and co-workers.1 These new ligands proved to be suitable for gener...
Keywords: Catalysis, Cross couplings, Ligands

Peer-Reviewed Papers
15

References

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