763381

Sigma-Aldrich

XPhos Pd G3

98%

Synonym(s):
XPhos-G3-Palladacycle, XPhos-Pd-G3, (2-Dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate
Empirical Formula (Hill Notation):
C46H62NO3PPdS
CAS Number:
Molecular Weight:
846.45
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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(C)C(C=C1C(C)C)=CC(C(C)C)=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.NC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5

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

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.

Packaging

250 mg in glass bottle
1, 5 g in glass bottle

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

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)
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