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764183

Sigma-Aldrich

APhos Pd G3

97%

Synonym(s):

APhos-Pd-G3, Palladium G3-(4-(N,N-Dimethylamino)phenyl)di-tert-butylphosphine, [4-(Di-tert-butylphosphino)-N,N-dimethylaniline-2-(2′-aminobiphenyl)]palladium(II) methanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C29H41N2O3PPdS
CAS Number:
Molecular Weight:
635.11
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

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

192-201 °C (decomposition)

functional group

phosphine

SMILES string

NC1=C(C=CC=C1)C2=C([Pd]OS(C)(=O)=O)C=CC=C2.CN(C)C3=CC=C(C=C3)P(C(C)(C)C)C(C)(C)C

InChI

1S/C16H28NP.C12H10N.CH4O3S.Pd/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h9-12H,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

SNUBBUQVCDWEAV-UHFFFAOYSA-M

Application

APhos Pd G3 is a Buchwald precatalyst that can be used in cross-coupling reactions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Capture of reactive monophosphine-ligated palladium (0) intermediates by mass spectrometry
Zheng Q, et al.
Journal of the American Chemical Society, 137(44), 14035-14038 (2015)
Synthesis of Double-Bond-Substituted Hemithioindigo Photoswitches
Gerwien A, et al.
Organic Letters, 20(1), 232-235 (2018)

Articles

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form.

Tools aid in kit setup for organic chemistry techniques, ensuring ease and success.

Tools aid in kit setup for organic chemistry techniques, ensuring ease and success.

Tools aid in kit setup for organic chemistry techniques, ensuring ease and success.

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Related Content

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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