638439

JohnPhos

97%

• Synonim(y): (2-Biphenyl)di-tert-butylphosphine, (2-Biphenylyl)di-tert-butylphosphine, 2-(Di-tert-butylphosphino)biphenyl
• Wzór liniowy: C₆H₅C₆H₄P[C(CH₃)₃]₂
• Numer CAS: 224311-51-7
• Masa cząsteczkowa: 298.40
• Beilstein: 8322131
• Numer MDL: MFCD01862440
• Kod UNSPSC: 12352002
• Identyfikator substancji w PubChem: 24882938
• NACRES: NA.22

Właściwości

• Poziom jakości: 100
• Próba: 97%
• przydatność reakcji: 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.)
• grupa funkcyjna: phosphine
• ciąg SMILES: 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
• Klucz InChI: CNXMDTWQWLGCPE-UHFFFAOYSA-N

Opis

Opis ogólny

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

Zastosowanie

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

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Informacja o środkach bezpieczeństwa

• Kod klasy składowania: 11 - Combustible Solids
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable
• Środki ochrony indywidualnej: Eyeshields, Gloves, type N95 (US)