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Documenti fondamentali

638099

Sigma-Aldrich

CyJohnPhos

97%

Sinonimo/i:

2-(Dicyclohexylphosphino)biphenyl, (2-Biphenyl)dicyclohexylphosphine, Cyclohexyl JohnPhos

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About This Item

Formula empirica (notazione di Hill):
C24H31P
Numero CAS:
Peso molecolare:
350.48
Beilstein:
8440533
Numero MDL:
Codice UNSPSC:
12352002
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: C-X Bond Formation

reagent type: ligand
reaction type: Hiyama Coupling

reagent type: ligand
reaction type: Methylations

reagent type: ligand
reaction type: Negishi Coupling

reagent type: ligand
reaction type: Oxidations

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Punto di fusione

102-106 °C (lit.)

Gruppo funzionale

phosphine

Stringa SMILE

C1CCC(CC1)P(C2CCCCC2)c3ccccc3-c4ccccc4

InChI

1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2
LCSNDSFWVKMJCT-UHFFFAOYSA-N

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Descrizione generale

CyJohnPhos [(2-Biphenyl)dicyclohexylphosphine] is an air-stable, bulky and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Learn more about Buchwald Phosphine Ligands

Applicazioni

CyJohnPhos may be used in combination with a nickel catalyst for the Suzuki-Miyaura arylation of tertiary benzylic acetates with aryl boroxines to produce diaryl and triaryl quaternary stereocenters.
Ligand employed in the palladium-catalysed synthesis of 1,3,5-tris(2′-aminophenyl)benzene, a core building block for potential ionic receptors.
Ligand for amination of aryl halides and triflates.

Note legali

Usage subject to US Patents 6307087 and 6395916.

Indicazioni di pericolo

Classi di pericolo

Aquatic Chronic 4

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

Eyeshields, Gloves, type N95 (US)


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I clienti hanno visto anche

Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity.
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Journal of the American Chemical Society, 138(37), 12057-12060 (2016)
Synlett, 2027-2027 (2006)
Daichi Kakizoe et al.
Dalton transactions (Cambridge, England : 2003), 46(43), 14804-14811 (2017-10-19)
We report the synthesis and photophysical properties of Cu(i) complexes with 1,10-phenanthroline (phen) and monodentate phosphine ligands. Single crystal X-ray structural analysis revealed that these have three-coordinated trigonal planar geometries. We also found that one of them, [Cu(phen)(Johnphos)]BF
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand

Articoli

Buchwald Phosphine Ligands

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

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