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940356

Sigma-Aldrich

GPhos Pd G3 ChemBeads

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Synonym(s):

Methanesulfonato[Dicyclohexyl[3-(1,1-dimethylethoxy)-6-methoxy-2′,6′-bis(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine](2′-amino-1,1′-biphenyl-2-yl)palladium(II) ChemBeads

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About This Item

Empirical Formula (Hill Notation):
C48H66NO5PPdS
CAS Number:
2489525-82-6
Molecular Weight:
906.50
UNSPSC Code:
12352100

form

solid

Quality Level

100

composition

, 4-6 wt. % (loading)

reaction suitability

reagent type: catalyst

SMILES string

O=S(O[Pd]([P](C1CCCCC1)(C2CCCCC2)C3=C(C4=C(C(C)C)C=CC=C4C(C)C)C(OC)=CC=C3OC(C)(C)C)C5=C(C6=C(N)C=CC=C6)C=CC=C5)(C)=O

InChI

InChI=1S/C35H53O2P.C12H10N.CH4O3S.Pd/c1-24(2)28-20-15-21-29(25(3)4)32(28)33-30(36-8)22-23-31(37-35(5,6)7)34(33)38(26-16-11-9-12-17-26)27-18-13-10-14-19-27;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h15,20-27H,9-14,16-19H2,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

PLMOFCQYSAAMKA-UHFFFAOYSA-M

General description

The ChemBeads product of the GPhos ligand combined with the Buchwald third Generation Palladacycle. The GPhos motif gives superb activity while having greater stability relative to other superbulky Buchwald ligands. Loaded at 5% wt. on glass beads for use in high-throughput expermentation (HTE). GPhos Pd G3 has been used in: - The production of chiral N-arylamines via a telescoped transaminase-Buchwald-Hartwig Amination cascade.

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 general uses, product is also available in powdered form (920460 )

Features and Benefits

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.

related product

Product No.
Description
Pricing

918008

GPhos, ≥95%

920479

GPhos Pd G4

920460

GPhos Pd G3

922900

GPhos Pd G6 TES

938750

GPhos ChemBeads

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Information

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Christian M Heckmann et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 27(67), 16616-16620 (2021-09-30)
The combination of biocatalysis and chemocatalysis can be more powerful than either technique alone. However, combining the two is challenging due to typically very different reaction conditions. Herein, chiral N-aryl amines, key features of many active pharmaceutical ingredients, are accessed
Scott D McCann et al.
Journal of the American Chemical Society, 142(35), 15027-15037 (2020-08-14)
We have developed a new dialkylbiaryl monophosphine ligand, GPhos, that supports a palladium catalyst capable of promoting carbon-nitrogen cross-coupling reactions between a variety of primary amines and aryl halides; in many cases, these reactions can be carried out at room
Bryan T Ingoglia et al.
Tetrahedron, 75(32), 4199-4211 (2020-01-04)
Over the past three decades, Pd-catalyzed cross-coupling reactions have become a mainstay of organic synthesis. In particular, catalysts derived from biaryl monophosphines have shown wide utility in forming C-N bonds under mild reaction conditions. This work summarizes a variety of
Noah P Tu et al.
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
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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