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932213

Sigma-Aldrich

XantPhos Pd G3 ChemBeads

Synonym(s):

[(4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C52H45NO4P2PdS
CAS Number:
Molecular Weight:
948.35
UNSPSC Code:
12352101
NACRES:
NA.22

form

solid

Quality Level

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

General description

XantPhos 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. XantPhos Pd G3 is an excellent reagent for palladium catalyzed 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

XantPhos Pd G3 may be used in the following processes:

Negishi cross-coupling reaction during the synthesis of palmerolides.
Aminocarbonylation of heteroaryl bromides with carbon monoxide (CO) in the presence of triethylamine.
Coupling between polyglycosyl thiols and aglycon halides by C-S bond formation.

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.

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Product is also available as neat precatalyst (763039)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Versatile Methods to Dispense Submilligram Quantities of Solids Using Chemical-Coated Beads for High-Throughput Experimentation
Martin, et al
Organic Process Research & Development, 23, 1900?1907-1900?1907 (2019)
High-Throughput Reaction Screening with Nanomoles of Solid Reagents Coated on Glass Beads
Tu, Noah P., et al.
Angewandte Chemie (International Edition in English), 58, 7987-7991 (2019)
Ana L Aguirre et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 27(51), 12981-12986 (2021-07-08)
High-throughput experimentation (HTE) methods are central to modern medicinal chemistry. While many HTE approaches to C-N and Csp2 -Csp2 bonds are available, options for Csp2 -Csp3 bonds are limited. We report here how the adaptation of nickel-catalyzed cross-electrophile coupling of

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