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763039

Sigma-Aldrich

XantPhos Pd G3

95%

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Synonym(s):
[(4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate
Empirical Formula (Hill Notation):
C52H45NO4P2PdS
CAS Number:
Molecular Weight:
948.35
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

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

164-167 °C (decomposition)

functional group

phosphine

SMILES string

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.CC3(C)c4cccc(P(c5ccccc5)c6ccccc6)c4Oc7c(cccc37)P(c8ccccc8)c9ccccc9

InChI

1S/C39H32OP2.C12H10N.CH4O3S.Pd/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h3-28H,1-2H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

Inchi Key

AJVXPGQYAKUTGX-UHFFFAOYSA-M

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This Item
763381762229794228
XantPhos Pd G3 95%

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763039

XantPhos Pd G3

XPhos Pd G3 98%, 1:1 MTBE adduct

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763381

XPhos Pd G3

tBuXPhos Pd G3 98%

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762229

tBuXPhos Pd G3

N-XantPhos Pd G3 95%

Sigma-Aldrich

794228

N-XantPhos Pd G3

form

solid

form

solid

form

solid

form

solid

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

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

reaction suitability

-

reaction suitability

-

mp

164-167 °C (decomposition)

mp

146-151 °C (decomposition)

mp

130-140 °C

mp

-

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

General description

XantPhos Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. XantPhos Pd G3 is an excellent reagent for palladium catalyzed cross-coupling reactions. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

XantPhos Pd G3 may be used in the following processes:
  • Negishi cross-coupling reaction during the synthesis of palmerolides.
  • Aminocarbonylation of heteroaryl bromides with carbon monoxide (CO) in the presence of triethylamine.
  • Coupling between polyglycosyl thiols and aglycon halides by C-S bond formation.
For small scale and high throughput uses, product is also available as ChemBeads (932213)

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


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A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15-C16 bond formation.
Carrillo J, et al.
Tetrahedron Letters, 55(33), 4623-4627 (2014)
Stereoretentive Palladium-Catalyzed Arylation, Alkenylation, and Alkynylation of 1-Thiosugars and Thiols Using Aminobiphenyl Palladacycle Precatalyst at Room Temperature.
Bruneau A, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 21(23), 8375-8379 (2015)
2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
Bruneau A, et al.
ACS Catalysis, 5(2), 1386-1396 (2015)

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