PMC2016
JohnPhos
≥98%, ISOM8™
Synonym(s):
JohnPhos, (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:
Molecular Weight:
298.40
UNSPSC Code:
12352002
Beilstein/REAXYS Number:
8322131
MDL number:
product line
ISOM8™
Quality Segment
assay
≥98%
form
solid
purified by
HPLC
reaction suitability
reagent type: ligand, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: C-X Bond Formation, reagent type: ligand
reaction type: Cross Couplings, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
mp
86-88 °C (Lit.), 86-88 °C (lit.)
application(s)
diagnostic assay manufacturing
life science and biopharma
functional group
phosphine
storage temp.
room temp
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
General description
Welcome to our ISOM8™ line of high-quality products available and able to scale for manufacturing. Within our ISOM8 team, we have expertise and documentation to support ISO 9001 industrial and non-GMP pharma production needs, as defined by our M-Clarity™ Program. Ourportfolio of ISOM8 products and chemistries is ever evolving to support ourvalued Sigma-Aldrich® customers′ requirements. Please navigateto our documents section to look at quality documentation for this product,provided with support of our Elevate Program.
Application
Ligand utilized in amination of aryl halides and aryl triflates.
Catalyst for:
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
JohnPhos is a sterically bulkybiarylphosphine ligand developed by Buchwald group . As areactive dialkylbiaryl phosphine ligand, it is primarily employed to facilitatepalladium-catalyzed cross-coupling reactions, including C-N bond-formingprocesses.
Notable Characteristics & Key Uses
Recent Studiesand Innovations:
Notable Characteristics & Key Uses
- Chemical Structure: JohnPhos is abidentate phosphine ligand made up of a diphenylphosphino group linked to abiaryl backbone. This structure allows it to bond with metal centers throughthe phosphorus atom, creating stable metal-ligand complexes.
- Sterically Bulky and Electron-Rich: Theligand has a biphenyl backbone with di-tert-butylphosphino groups. This designcreates significant steric hindrance and high electron density, which helpsimprove catalysis.
- High Reactivity: It is knownfor enabling difficult transformations, especially in palladium-catalyzedcouplings.
- Air-Stable Solid: JohnPhos is awhite powder that can be stored in the air, making it easy to work with.
- Reaction Suitability: It workswell in Suzuki-Miyaura coupling, Buchwald-Hartwig amination, and Heck reactiontypes.
- Catalysis: Generally used inpalladium-catalyzed cross-coupling reactions, improving efficiency andselectivity. Facilitates challenging couplings, including the arylation ofolefins with aryl chlorides and decarbonylative couplings.
- Organic Synthesis: Enables thesynthesis of complex organic molecules, involving pharmaceuticals and finechemicals.
- Material Science: Used in the innovating of new materials like polymersand nanocomposites.
Recent Studiesand Innovations:
- SelectiveGold(I) Complex Formation: TheJohnPhos ligand selectively coordinates to gold(I) complexes, forming highlystable intermediates. The steric protection afforded by JohnPhos isinstrumental in stabilizing reactive species during catalysis (Leung et al., 2020).
- EnhancedCatalytic Activity in Multimetal Systems: The incorporation of JohnPhos into metal complexes -including Au(I), Ag(I), Cu(I), and Pd(II) - with acenaphthylene dramaticallyincreases catalytic activity in hydrofunctionalization and cross-couplingreactions by enabling unique spatial geometries at the metal center (Victoria et al., 2024)
Legal Information
ISOM8 is a trademark of Sigma-Aldrich Co. LLC
M-CLARITY is a trademark of Merck KGaA, Darmstadt, Germany
SIGMA-ALDRICH is a registered trademark of Merck KGaA, Darmstadt, Germany
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Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
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