XantPhos Pd G4

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Cat Number

CHE1621274198

CAS Number

1621274-19-8

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Product Detail Description Scientific Support Customer Q&A

CAS Number

1621274-19-8

Synonyms

Methanesulfonato[4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene](2'-methylamino-1,1'-biphenyl-2-yl)palladium(II); Methanesulfonato[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene](2'-methylamino-1,1'-biphenyl-2-yl)palladium(II)

Molecular Formula

C92H78NO8P4PdS2-

Molecular Weight

1620.05

Smiles

[Pd](O[S](=O)(=O)C)c8c(cccc8)c9c(cccc9)NC.P(c7ccccc7)(c6ccccc6)c1c2c(ccc1)C(c3c(c(ccc3)P(c5ccccc5)c4ccccc4)O2)(C)C

General Description

XantPhos Pd G4 is the fourth generation Buchwald precursor based on the Xantphos ligand. It is a highly advanced organometallic complex optimized for practical cross-coupling under mild conditions. This reagent offers the unique benefits of solid-state stability to air and moisture allowing easy handling during HTS and large scale syntheses where dependable catalytic activity is necessary.

Mechanism of Action

XantPhos Pd G4 takes advantage of a methanesulfonate counterion and an aminobiphenyl backbone that undergoes facile reductive elimination so as not to generate any inhibitory side products. This leaves a high concentration of catalysts available to participate in the catalytic cycle leading to improved reaction rates, allowing even difficult or sterically demanding substrates to couple.

Application

Due to its incredible versatility XantPhos Pd G4 has become an extremely popular precatalyst used in the pharmaceutical industries for C-N cross coupling and carbon oxygen bond formation. Its distinct bite angle renders this catalyst ideal for the amination of aryl halides with primary amines as well as complex heterocycle formation. The catalyst has also been used for the development of functional materials and late-stage modifications of bioactives.

At 1-40 bar CO and 50-120 ℃, the in situ generated pre-catalyst from Pd(OAc)₂/XantPhos or the commercial XantPhos Pd G4 source could be successfully applied to five transformations: (i) selective mono-aminocarbonylation of 6-iodoquinoline to afford 6-carboxamidoquinolines; (ii) double carbonylation under high pressure to give 6-glyoxylamidoquinolines; (iii) one-pot aminocarbonylation/cyclization of 3-bromo-2-iodoquinoline to N-substituted pyrrolo[3,4-b]quinoline-1,3-diones; (iv) chemodivergent coupling of 3-iodochromone with secondary amines to chromone-3-carboxamides and primary amines to unprecedented chroman-2,4-diones through an ANRORC rearrangement motif; (v) amino- or aryloxy-carbonylation of 3-iodoflavone to give C3-functionalized flavones.
Turnover numbers as high as 200 were obtained using XantPhos Pd G4. The reaction tolerated ester, alcohol, heterocycle, and phenol substituents and gram-scale quantities of crystalline product could be obtained for all examples, which were authenticated by X-ray diffraction studies. Mechanistic investigation showed that the bulky bite angle and electron-rich character of XantPhos facilitates oxidative addition and CO insertion, quells β-hydride elimination and funnels the reaction to mono- or double-carbonylation depending on the CO pressure and identity of the amine.

Fig. 1 Synthesis of Butoxycaine from CO₂ via electroreduction and Pd-catalyzed alkoxycarbonylation. (Sami C. 2025)

References

Sami C.; et al. Palladium-catalyzed carbonylation reactions for late-stage functionalization of privileged heterocyclic scaffolds. 2025.

Does XantPhos Pd G4 require an external ligand addition?

No, the ligand is already coordinated to the palladium center in a 1:1 ratio, ensuring the correct stoichiometry for the active catalytic species.

Is XantPhos Pd G4 air sensitive?

The product is air stable as a solid. However, we suggest an inert atmosphere for storage and reaction conditions to ensure long-term stability and optimal reaction results.

What solvents work well with XantPhos Pd G4?

It is readily soluble in common organic solvents. Examples include THF, toluene, dioxane, and DME.

Can XantPhos Pd G4 be used with functional groups?

Xantphos Pd G4 has been shown to tolerate many functional groups.