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936952

Sigma-Aldrich

BrettPhos Pd G4 ChemBeads

Synonym(s):

(SP-4-3)-[Dicyclohexyl[3,6-dimethoxy-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine-κP](methanesulfonato-κO)[2′-(methylamino-κN)[1,1′-biphenyl]-2-yl-κC]

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About This Item

Empirical Formula (Hill Notation):
C49H68NO5PPdS
CAS Number:
Molecular Weight:
920.53
UNSPSC Code:
12352100
NACRES:
NA.22

form

solid

Quality Level

composition

, ~5 wt. % (loading of catalyst)

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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

SMILES string

CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C(OC)=CC=C2OC.CNC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5

InChI

1S/C35H53O2P.C13H12N.CH4O3S.Pd/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h19-25,27-28H,9-18H2,1-8H3;2-7,9-10,14H,1H3;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

YVIWYUQZBYFFLZ-UHFFFAOYSA-M

General description

BrettPhos Pd G4 is an N-substituted 2-aminobiphenylpalladium methanesulfonate precatalyst. It is a fourth generation (G4) Buchwald precatalyst that is similar to the third generation (G3) precatalysts except that the amino group on the biphenyl backbone is methylated. This modification helps to prevent the limitations of using the third generation precatalysts. It is air, moisture and thermally-stable and shows good solubility in common organic solvents. BrettPhos Pd G4 is highly useful in cross-coupling reactions. Some of its excellent features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

For larger scale uses, product also available in powdered form 804355

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


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Angewandte Chemie (International ed. in English), 58(24), 7987-7991 (2019-03-21)
Technologies that enable rapid screening of diverse reaction conditions are of critical importance to methodology development and reaction optimization, especially when molecules of high complexity and scarcity are involved. The lack of a general solid dispensing method for chemical reagents

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