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Xantphos Pd G3
[CAS# 1445085-97-1]

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Identification
Classification Organic raw materials >> Organic phosphine compound
Name Xantphos Pd G3
Synonyms [2'-(Amino)[1,1'-biphenyl]-2-yl][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine](methanesulfonato)palladium
Molecular Formula C52H45NO4P2PdS
Molecular Weight 948.35
CAS Registry Number 1445085-97-1
EC Number 811-348-5
SMILES CC1(c2cccc(c2Oc3c1cccc3P(c4ccccc4)c5ccccc5)P(c6ccccc6)c7ccccc7)C.CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N
Properties
Melting Point 164-167 ºC (decomp.)
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H302-H315-H319-H332-H335    Details
Precautionary Statements P261-P280-P305+P351+P338    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
Eye irritationEye Irrit.2AH319
Eye irritationEye Irrit.2H319
SDS Available
up Discovory and Applicatios
Xantphos Pd G3 is an advanced palladium-based catalyst complex designed to enhance the efficiency of various organic transformations. It incorporates Xantphos, a renowned phosphine ligand known for its exceptional catalytic properties, paired with palladium to form a robust catalyst used in numerous chemical reactions.

The discovery of Xantphos Pd G3 stems from the need to improve catalytic systems for complex organic syntheses. Xantphos itself is a bisphosphine ligand featuring a unique structure that provides both steric and electronic effects conducive to stable and reactive palladium complexes. The "G3" designation refers to the third generation or specific variant of Xantphos, indicating refinements aimed at optimizing its performance.

The development of Xantphos Pd G3 was driven by the desire to create a palladium complex that could offer enhanced activity and selectivity in key reactions such as cross-coupling processes. Xantphos Pd G3 is particularly noted for its role in palladium-catalyzed coupling reactions, including the Suzuki-Miyaura, Heck, and Buchwald-Hartwig reactions. These processes are crucial for forming carbon-carbon and carbon-heteroatom bonds, making them valuable in the synthesis of pharmaceuticals, agrochemicals, and advanced materials.

In application, Xantphos Pd G3 is used to improve reaction rates, yields, and selectivity. The Xantphos ligand stabilizes the palladium center and influences its reactivity, allowing for more efficient and controlled catalytic processes. This makes Xantphos Pd G3 a valuable tool for chemists seeking to streamline synthetic routes and achieve high-purity products.

The significance of Xantphos Pd G3 lies in its ability to facilitate challenging reactions with precision. For instance, it has been shown to enhance the coupling efficiency in the synthesis of complex organic molecules, enabling the creation of structures that might otherwise be difficult to obtain. This capability is particularly important in the pharmaceutical industry, where the precision of chemical synthesis can impact drug development and production.

Overall, Xantphos Pd G3 exemplifies advancements in catalytic chemistry, providing a powerful tool for improving synthetic efficiency and selectivity. Its development reflects ongoing efforts to optimize palladium-based catalysts and expand their applications in organic synthesis.

References

2020. Air- and moisture-stable Xantphos-ligated palladium dialkyl complex as a precatalyst for cross-coupling reactions. Chemical Communications, 56(3).
DOI: 10.1039/C9CC06946A

2021. Rapid 18F-labeling via Pd-catalyzed S-arylation in aqueous medium. Chemical Communications, 57(29).
DOI: 10.1039/D1CC00745A

2021. Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA. Chemical Science, 12(16).
DOI: 10.1039/D1SC00789K
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