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900608

Sigma-Aldrich

APhos Pd G4

95%

Synonym(s):

(Methanesulfonato-κO)[2′-(methylamino)-2-biphenylyl]palladium - 4-[bis(2-methyl-2-propanyl)phosphino]-N,N-dimethylaniline

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About This Item

Empirical Formula (Hill Notation):
C30H43N2O3PPdS
CAS Number:
2812444-73-6
Molecular Weight:
649.13
UNSPSC Code:
12161600
NACRES:
NA.22

Quality Level

100

Assay

95%

form

powder or crystals

feature

generation 4

reaction suitability

core: palladium
reagent type: catalyst
reaction type: Cross Couplings

mp

204 °C

SMILES string

O=S(=O)([O-][Pd+2]1([C-]=2C=CC=CC2C=3C=CC=CC3[NH]1C)[P](C4=CC=C(C=C4)N(C)C)(C(C)(C)C)C(C)(C)C)C

InChI

1S/C16H28NP.C13H12N.CH4O3S.Pd/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h9-12H,1-8H3;2-7,9-10,14H,1H3;1H3,(H,2,3,4);/q;-1;;+2/p-1

InChI key

MLEINNWTBGCQPS-UHFFFAOYSA-M

Related Categories

Application

APhos Pd G4 is a powerful ligand for classic cross-coupling reactions combined with the Buchwald Fourth Generation Palladacycle. Bench stable, soluble in most organic solvents.

Storage Class Code

11 - Combustible Solids

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Nathaniel H Park et al.
Angewandte Chemie (International ed. in English), 54(28), 8259-8262 (2015-06-03)
In Pd-catalyzed C-N cross-coupling reactions, α-branched secondary amines are difficult coupling partners and the desired products are often produced in low yields. In order to provide a robust method for accessing N-aryl α-branched tertiary amines, new catalysts have been designed

Articles

G3 and G4 Buchwald Precatalysts

G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

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Buchwald Group – Professor Product Portal

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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