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Key Documents

638099

Sigma-Aldrich

CyJohnPhos

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C24H31P
CAS Number:
Molecular Weight:
350.48
Beilstein:
8440533
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

Quality Level

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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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.[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.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Hazard Statements

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)
    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.
    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
    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

    Articles

    Buchwald Ligands

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

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