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638099

Sigma-Aldrich

CyJohnPhos

97%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C24H31P
Número de CAS:
247940-06-3
Peso molecular:
350.48
Beilstein:
8440533
Número MDL:
MFCD01862441
Código UNSPSC:
12352002
ID de la sustancia en PubChem:
24882909
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

100

Ensayo

97%

idoneidad de la reacción

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

mp

102-106 °C (lit.)

grupo funcional

phosphine

cadena SMILES

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

Clave InChI

LCSNDSFWVKMJCT-UHFFFAOYSA-N

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Descripción general

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

Aplicación

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.[1]
Ligand employed in the palladium-catalysed synthesis of 1,3,5-tris(2′-aminophenyl)benzene, a core building block for potential ionic receptors.[2]
Ligand for amination of aryl halides and triflates.

Información legal

Usage subject to US Patents 6307087 and 6395916.

Frases de peligro

H413

Clasificaciones de peligro

Aquatic Chronic 4

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
STBL3485
STBL1895
STBL1891
SHBQ3474
STBK5407

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Synlett, 2027-2027 (2006)
Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity.
Zhou Q, et al.
Journal of the American Chemical Society, 138(37), 12057-12060 (2016)
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
Ruben Martin et al.
Accounts of chemical research, 41(11), 1461-1473 (2008-07-16)
The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon-carbon
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
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Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

Buchwald Ligands

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

Buchwald Ligands

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

Buchwald Ligands

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

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