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804959

Sigma-Aldrich

DavePhos-Pd-G3

95%

Synonym(s):

Methanesulfonato 2-dicyclohexylphosphino-2-(N,N-dimethylamino)biphenyl(2′-amino-1,1′-biphenyl-2-yl) palladium(II)

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About This Item

Empirical Formula (Hill Notation):
C39H49N2O3PPdS
CAS Number:
Molecular Weight:
763.28
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

Quality Level

Assay

95%

form

solid

feature

generation 3

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Cross Couplings

impurities

<5% THF

mp

183-200 °C (decomp)

functional group

phosphine

SMILES string

CN(C)C1=C(C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2)C=CC=C1.NC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5

InChI

1S/C26H36NP.C12H10N.CH4O3S.Pd/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h9-12,17-22H,3-8,13-16H2,1-2H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

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1 of 4

This Item
936960763004745979
reaction suitability

core: palladium, reaction type: Heck Reaction, reaction type: Negishi Coupling, reaction type: Stille Coupling, reagent type: catalyst
reaction type: Cross Couplings, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Sonogashira Coupling, reaction type: Hiyama Coupling, reaction type: Suzuki-Miyaura Coupling

reaction suitability

-

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Cross Couplings

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Cross Couplings

functional group

phosphine

functional group

-

functional group

phosphine

functional group

phosphine

form

solid

form

solid

form

solid

form

solid

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

183-200 °C (decomp)

mp

-

mp

176-178 °C (decomposition)

mp

119-131 °C

General description

DavePhos-Pd-G3 is a modified G3 precatalyst (G3′). It has been synthesized by Buchwald and coworkers from second generation (G2) precatalyst by methylation of the amino group present on biphenyl backbone. It is a useful catalyst for various cross-coupling reactions. They are versatile catalysts. They have long life in solutions and are readily soluble in various organic solvents. G3- precatalysts have been employed in various C-N bond forming reactions.[1]

Application

Pd precatalyst for cross-coupling

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Carc. 2

Supplementary Hazards

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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    2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
    Bruneau A, et al.
    ACS Catalysis, 5(2), 1386-1396 (2015)

    Articles

    All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

    All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

    All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

    G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

    Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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