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900620

Sigma-Aldrich

4MetBuXPhos Pd G3

Synonym(s):

Methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II)

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About This Item

Empirical Formula (Hill Notation):
C46H66NO3PPdS
CAS Number:
Molecular Weight:
850.48
MDL number:
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder

Quality Level

feature

generation 3

reaction suitability

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

functional group

phosphine

SMILES string

O=S(=O)([O-][Pd+2]1([C-]=2C=CC=CC2C=3C=CC=CC3[NH2]1)[P](C4=C(C=5C(=CC(=CC5C(C)C)C(C)C)C(C)C)C(=C(C(=C4C)C)C)C)(C(C)(C)C)C(C)(C)C)C

InChI

InChI=1S/C33H53P.C12H10N.CH4O3S.Pd/c1-19(2)26-17-27(20(3)4)30(28(18-26)21(5)6)29-24(9)22(7)23(8)25(10)31(29)34(32(11,12)13)33(14,15)16;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h17-21H,1-16H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;-1;;+2/p-1

InChI key

XHETXDRRRUEBJH-UHFFFAOYSA-M

Application

4MetBuXPhos Pd G3 is a third generation (G3) Buchwald palladium precatalyst for cross-coupling, demonstrating improved stability and reactivity from previous generations. This same product was formerly listed under RNI00184.

related product

Product No.
Description
Pricing

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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Articles

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.

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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