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CyJohnPhos

Name: CyJohnPhos
Brand: ALDRICH

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₂₄H₃₁P

CAS Number:

247940-06-3

Molecular Weight:

350.48

Beilstein:

8440533

MDL number:

MFCD01862441

PubChem Substance ID:

24882909

NACRES:

NA.22

Quality Level

100

Assay

97%

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: 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.)

functional group

phosphine

SMILES string

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

InChI key

LCSNDSFWVKMJCT-UHFFFAOYSA-N

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Related Categories

Buchwald Catalysts & Ligands

Phosphine Ligands

General description

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

Application

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.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Hazard Statements

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)

Photophysical properties of three coordinated copper(i) complexes bearing 1,10-phenanthroline and a monodentate phosphine ligand.

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

Biaryl phosphane ligands in palladium-catalyzed amination.

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

Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

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