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900349

Sigma-Aldrich

cataCXium Pd G4

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Synonym(s):
[di(adamantan-1-yl)(butyl)phosphine](methanesulfonato-κO)[2′-(methylamino)-2-biphenylyl]palladium
Empirical Formula (Hill Notation):
C38H54NO3PPdS
CAS Number:
2230788-67-5
Molecular Weight:
742.30
UNSPSC Code:
12352103
PubChem Substance ID:
329769810
NACRES:
NA.22

form

powder

Quality Level

100

feature

generation 4

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

CCCCP([C@@]12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3)[C@@]4(C5)C[C@H]6C[C@H](C[C@@H]5C6)C4.CNC7=C(C8=CC=CC=C8[Pd]OS(C)(=O)=O)C=CC=C7

InChI

1S/C24H39P.C13H12N.CH4O3S.Pd/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h17-22H,2-16H2,1H3;2-7,9-10,14H,1H3;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

ROZFJYIWIVSDBR-UHFFFAOYSA-M

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Application

A fourth generation (G4) Buchwald precatalyst that is similar to the third generation (G3) precatalysts except that the amino group on the biphenyl backbone is methylated. This modification helps to prevent the limitations found when using the third generation precatalysts. It is air, moisture, and thermally-stable and shows good solubility in common organic solvents.

WGK

WGK 3

Certificates of Analysis (COA)

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[Rupture of the pregnant uterus].
I Pardini et al.
Rivista italiana di ginecologia, 58(6), 481-502 (1977-11-01)

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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