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638439

JohnPhos

97%

Synonym(s):

(2-Biphenyl)di-tert-butylphosphine, (2-Biphenylyl)di-tert-butylphosphine, 2-(Di-tert-butylphosphino)biphenyl

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$67.30

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$320.00

25 G

$811.00

$67.30


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About This Item

Linear Formula:
C6H5C6H4P[C(CH3)3]2
CAS Number:
Molecular Weight:
298.40
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
8322131

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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

Quality Level

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638099695874675938
assay

97%

assay

97%

assay

-

assay

96%

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: C-X Bond Formation, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Heck Reaction

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: C-X Bond Formation, reagent type: ligand
reaction type: Hiyama Coupling, reagent type: ligand
reaction type: Methylations, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Oxidations, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

reaction suitability

-

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

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

86-88 °C (lit.)

mp

102-106 °C (lit.)

mp

114-118 °C

mp

168-172 °C

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.[1] Coordination chemistry of gold catalysts bearing JohnPhos as ligand has been investigated by NMR spectroscopy.[2]

Learn more about Buchwald Phosphine Ligands

Application

Bulky biarylphosphine ligand utilized in the palladium catalyzed Stille cross-coupling reaction.[3]
JohnPhos, a bulky phosphine ligand, was employed as catalyst in the following studies:
  • Hydrophenoxylation of unactivated internal alkynes.[4]
  • Microwave-mediated Suzuki-Miyaura cross-coupling of benzylic bromides.[5]
  • Pharmaceutical synthesis of novel imidazo[1,2-a]pyridines, having potent activity against the herpes virus.[6]
  • Barluenga′s coupling of vinyl bromides with hydrazines.[6]
  • Pd-catalyzed 2,3-diarylation of α,α-disubstituted-3-thiophenemethanols, via cleavage of C-H and C-C bonds.[7]
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

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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Artamkina, Galina A.; et al.
Synlett, 2, 235-238 (2006)
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
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.
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
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

Articles

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

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

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

Buchwald Phosphine Ligands

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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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