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638439

Sigma-Aldrich

(2-Biphenyl)di-tert-butylphosphine

97%

Sinónimos:

(2-Biphenylyl)di-tert-butylphosphine

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About This Item

Fórmula lineal:
C6H5C6H4P[C(CH3)3]2
Número de CAS:
224311-51-7
Peso molecular:
298.40
Beilstein/REAXYS Number:
8322131
MDL number:
MFCD01862440
UNSPSC Code:
12352002
PubChem Substance ID:
24882938
NACRES:
NA.22

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

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Categorías relacionadas

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
STBK1868
STBK1867
STBJ9089
SHBL3191
STBJ5738

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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
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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The Pd-catalyzed C–N bond formation has become an important synthetic reaction in the past 20 years. Several research groups have investigated this reaction and developed very versatile catalysts. Buchwald and coworkers have been very active in synthesizing and developing a portfolio of phosphine ligands for this transformation and other cross-coupling reactions.

Buchwald Ligands

Buchwald Ligands

Buchwald Phosphine Ligands

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Organosilanes for Cross-coupling

Over the past several years, Pd-catalyzed cross-coupling of silicon compounds has rapidly gained acceptance as a suitable alternative to more commonly known methods such as: Stille (Sn), Kumada (Mg), Suzuki (B), and Negishi (Zn) cross-couplings.

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