638439

(2-Biphenyl)di-tert-butylphosphine

97%

• Sinónimos: (2-Biphenylyl)di-tert-butylphosphine
• Fórmula lineal: C₆H₅C₆H₄P[C(CH₃)₃]₂
• Número de CAS: 224311-51-7
• Peso molecular: 298.40
• Beilstein/REAXYS Number: 8322131
• MDL number: MFCD01862440
• UNSPSC Code: 12352002
• PubChem Substance ID: 24882938
• NACRES: NA.22

Propiedades

• Quality Level: 100
• 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

Descripción

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

Información de seguridad

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)