Skip to Content
Merck
CN

Key Documents

View All Documentation

638439

JohnPhos

97%

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

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
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

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

Still not finding the right product?

Explore all of our products under JohnPhos

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SDBB5066
SDBB5059
SDBB5055
STBL2795
STBL2794

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

Buchwald Ligands

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

Buchwald Phosphine Ligands

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

Buchwald Ligands

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

View All Articles

Related Content

Buchwald Portfolio - Precatalysts and Ligands

Buchwald Portfolio: Palladacycles and Ligands

Digital Reaction Optimization with Catalexis

Accelerate catalyst and ligand screening with Catalexis integrated with BayBE™ for fast, cost-effective reaction optimization across benchtop and HTE workflows.

利用Catalexis进行数字反应优化

通过将 Catalexis 与 BayBE™ 集成，加速催化剂和配体的筛选，从而在台式和 HTE 工作流程中实现快速、经济高效的反应优化。

View All Related Content
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.
View All Related Papers

Global Trade Item Number

SKUGTIN
638439-25G04061833399354
638439-5G04061833357019
638439-1G04061832726700
638439-100G04061833301548