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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:
1507403-85-1
Molecular Weight:
850.48
MDL number:
MFCD28009172
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder

Quality Level

100

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.

Other Notes

G3 and G4 Buchwald Precatalysts

related product

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW5532
MKCW3133
SHBN6778
SHBN0350
MKCD2917

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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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