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Key Documents

638021

Sigma-Aldrich

DavePhos

97%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C26H36NP
Numero CAS:
Peso molecolare:
393.54
Numero MDL:
Codice UNSPSC:
12352116
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

97%

Impiego in reazioni chimiche

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

Punto di fusione

121-124 °C (lit.)

Gruppo funzionale

phosphine

Stringa SMILE

CN(C)c1ccccc1-c2ccccc2P(C3CCCCC3)C4CCCCC4

InChI

1S/C26H36NP/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/h9-12,17-22H,3-8,13-16H2,1-2H3
ZEMZPXWZVTUONV-UHFFFAOYSA-N

Applicazioni

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.

Learn more about Buchwald Phosphine Ligands
Useful ligand for Pd-catalyzed C-N bond formation; amination of aryl halides containing hydroxyl, amide, or enolizable ketones.

Note legali

Usage subject to US Patents 6307087 and 6395916.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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Palladium-catalyzed benzylic CH insertion of 2-substituted N-iminopyridinium ylides.
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Organic Letters, 10(8), 1641-1643 (2008)
Palladium-catalyzed Negishi a-arylation of alkylsulfones.
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Articoli

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

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