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638439

Sigma-Aldrich

JohnPhos

97%

Synonym(s):

(2-Biphenyl)di-tert-butylphosphine, (2-Biphenylyl)di-tert-butylphosphine, 2-(Di-tert-butylphosphino)biphenyl

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About This Item

Linear Formula:
C6H5C6H4P[C(CH3)3]2
CAS Number:
Molecular Weight:
298.40
Beilstein:
8322131
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: C-X Bond Formation

reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

86-88 °C (lit.)

functional group

phosphine

SMILES string

CC(C)(C)P(c1ccccc1-c2ccccc2)C(C)(C)C

InChI

1S/C20H27P/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16/h7-15H,1-6H3

InChI key

CNXMDTWQWLGCPE-UHFFFAOYSA-N

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General description

JohnPhos is a Buchwald′s sterically bulky biaryl phosphine ligand. It is a reactive dialkylbiaryl phosphine ligand which catalyzes the carbon-nitrogen bond-forming reactions. Coordination chemistry of gold catalysts bearing JohnPhos as ligand has been investigated by NMR spectroscopy.

Learn more about Buchwald Phosphine Ligands

Application

Bulky biarylphosphine ligand utilized in the palladium catalyzed Stille cross-coupling reaction.
JohnPhos, a bulky phosphine ligand, was employed as catalyst in the following studies:
  • Hydrophenoxylation of unactivated internal alkynes.
  • Microwave-mediated Suzuki-Miyaura cross-coupling of benzylic bromides.
  • Pharmaceutical synthesis of novel imidazo[1,2-a]pyridines, having potent activity against the herpes virus.
  • Barluenga′s coupling of vinyl bromides with hydrazines.
  • Pd-catalyzed 2,3-diarylation of α,α-disubstituted-3-thiophenemethanols, via cleavage of C-H and C-C bonds.
Ligand utilized in amination of aryl halides and aryl triflates.

Catalyst for:
  • Decarboxylative cross-coupling of dialkoxybenzoic acids with diaryl disulfides or diaryl diselenides
  • Stereoselective preparation of imidazolidinones via intramolecular hydroamination of N-allylic-N-arylureas
  • Regioselective arylation of olefins with aryl chlorides
  • Cross-coupling reaction for the synthesis of polyunsaturated macrolactones
  • Regioselective O-alkylation reactions
  • Sonogashira-type cross coupling

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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