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Sigma-Aldrich

(2-Biphenyl)di-tert-butylphosphine

97%

Synonyme(s) :

(2-Biphenylyl)di-tert-butylphosphine

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About This Item

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

Niveau de qualité

100

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

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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

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)

Certificats d'analyse (COA)

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Steven W McDaniel et al.
Tetrahedron letters, 52(43), 5656-5658 (2011-10-04)
A procedure for benzylic Suzuki-Miyaura cross-coupling under microwave conditions has been developed. These conditions allowed for heterocyclic compounds to be coupled. Optimum conditions found were Pd(OAc)(2), JohnPhos as the catalyst and ligand, potassium carbonate as base, and DMF as the
Artamkina, Galina A.; et al.
Synlett, 2, 235-238 (2006)
Alexander Zhdanko et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(46), 14732-14744 (2012-09-29)
Coordination chemistry of gold catalysts bearing eight different ligands [L=PPh(3), JohnPhos (L2), Xphos (L3), DTBP, IMes, IPr, dppf, S-tolBINAP (L8)] has been studied by NMR spectroscopy in solution at room temperature. Cationic or neutral mononuclear complexes LAuX (L=L2, L3, IMes
Marcia E Richard et al.
Beilstein journal of organic chemistry, 9, 2002-2008 (2013-11-10)
A range of arylgold compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos
Masaya Nakano et al.
The Journal of organic chemistry, 71(21), 8309-8311 (2006-10-10)
Alpha,alpha-disubstituted 3-thiophenemethanols undergo selective diarylation accompanied by cleavage of the C-H and C-C bonds of the 2- and 3-positions, respectively, upon treatment with aryl bromides in the presence of a palladium catalyst to give the corresponding 2,3-diarylthiophenes in good yields.
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Buchwald Ligands

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

Buchwald Ligands

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

Buchwald Ligands

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

Buchwald Ligands

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

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Contenu apparenté

Plateforme de criblage de catalyseurs Catalexis

La plateforme Catalexis améliore la catalyse en optimisant numériquement la sélection des catalyseurs afin d'identifier les ligands phosphines les plus efficaces pour les réactions de couplage croisé.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

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