638439

(2-Biphenyl)di-tert-butylphosphine

97%

• Synonyme(s) : (2-Biphenylyl)di-tert-butylphosphine
• Formule linéaire : C₆H₅C₆H₄P[C(CH₃)₃]₂
• Numéro CAS: 224311-51-7
• Poids moléculaire : 298.40
• Numéro Beilstein : 8322131
• Numéro MDL: MFCD01862440
• Code UNSPSC : 12352002
• ID de substance PubChem : 24882938
• Nomenclature NACRES : NA.22

Propriétés

• Pureté: 97%
• Capacité de réaction: reaction type: Cross Couplings
• Pertinence de la réaction: 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
• Pf: 86-88 °C (lit.)
• Groupe fonctionnel: phosphine
• Chaîne 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
• Clé InChI: CNXMDTWQWLGCPE-UHFFFAOYSA-N

Description

Description générale

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

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)