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638439

JohnPhos

Name: JohnPhos
Brand: ALDRICH

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:

224311-51-7

Molecular Weight:

298.40

UNSPSC Code:

12352002

NACRES:

NA.22

PubChem Substance ID:

24882938

MDL number:

MFCD01862440

Beilstein/REAXYS Number:

8322131

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Properties

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

Description

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

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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Articles

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.