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Sigma-Aldrich

XPhos Pd G3

98%, 1:1 MTBE adduct

Sinónimos:

(2-Dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate, XPhos-G3-Palladacycle, XPhos-Pd-G3

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About This Item

Fórmula empírica (notación de Hill):
C46H62NO3PPdS
Número de CAS:
1445085-55-1
Peso molecular:
846.45
MDL number:
MFCD22666043
UNSPSC Code:
12352300
PubChem Substance ID:
329767048
NACRES:
NA.22

Quality Level

100

assay

98%

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

mp

146-151 °C (decomposition)

functional group

phosphine

SMILES string

CC(C1=CC(C(C)C)=C(C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C(C)C)=C1)C.NC5=C(C=CC=C5)C6=C(C=CC=C6)[Pd]OS(C)(=O)=O

InChI

1S/C33H49P.C12H10N.CH4O3S.Pd/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

NKKHABPORDUWIG-UHFFFAOYSA-M

Categorías relacionadas

General description

XPhos Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. XPhos Pd G3 is an excellent reagent for Suzuki cross-coupling reactions. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

XPhos Pd G3 may be used in the following reactions:
  • Cyanation reaction of heterocyclic halides.
  • Coupling of heteroaryl chlorides with polyfluoroaryl zinc reagents.
  • Coupling of 2,6-difluorophenylboronic acid with (hetero)aryl chlorides.
For small scale and high throughput uses, product is also available as ChemBeads (927783)

related product

Referencia del producto
Descripción
Precios

903027

QPhos Pd G3

903701

tBuDavePhos Pd G3, 1:1 THF adduct

905607

(R)-Tol-BINAP Pd G3, ≥95%

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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)

Artículos

Scale-Up Guide: Suzuki-Miyaura Cross-Coupling Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form.

KitAlysis™ Suzuki-Miyaura Cross-Coupling Reaction Screening Kit

Multiple tools have been created to ensure your success with kit set up. Start with the more detailed guide to ensure you are comfortable with all of the steps before using the quick guides on the excel worksheet. Remember that while the technique is new, it is still organic chemistry and so the steps will seem easy once you try just one kit. It is just a new way of approaching something you are already very good at.

KitAlysis High-Throughput Palladium Precatalyst Cross-Coupling Reaction Screening Kit

Materials Included in your KITALYSIS-24PD-2PK High-Throughput Screening Kit

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

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.

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