XPhos Pd G3

• CAS: 1445085-55-1
• Catalog Number: ACM1445085551-1
• Category: Palladium series catalysts
• Molecular Weight: 846.46
• Molecular Formula: C46H62NO3PPdS
• Synonyms: Methanesulfonato(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)
• Melting Point: 146-151 °C
• Appearance: Powder
• Application: Palladium precatalyst for facile C-N cross-coupling reactions.
• MDL Number: MFCD22666043

Case Study

Multigram-Scale Synthesis of Third-Generation Buchwald Precatalysts Containing Xphos

Sotnik, Svitlana O., et al. Molecules, 2021, 26(12), 3507.

XPhos Pd G3 is a catalyst used in organic synthesis, particularly in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig reactions. It is a highly efficient and air-stable catalyst that contains palladium as its active metal. XPhos Pd G3 is known for its ability to promote reactions under milder conditions and provide excellent yields and selectivity.
Synthesis of XPhos Pd G3
· A two-necked 2 L round bottom Schlenk flask equipped was charged with [Pd(ABP)(OMs)]2 (53.6 g, 64 mmol, 0.5 eq.) and XPhos (61.5 g, 129 mmol, 1 eq.). The flask was capped, three times evacuated and backfilled with argon.
· Anhydrous and deoxygenated tetrahydrofuran (1.4 L) were added in the flask under argon counterflow. The reaction mixture was stirred at room temperature for 1.5 h and then it was filtered under argon atmosphere.
· About 1.2 L of the filtrate was evaporated under vacuum via a rotor evaporator. Deoxygenated hexane (1.2 L) was added to the dark brown residue and the formation of a beige precipitate was observed.
· The flask was placed in an ultrasonic bath and sonicated for 20 min. A beige precipitate was filtered, washed with hexane (3× 250 mL) and dried under vacuum at 50 °C for 1 h to obtain 92.0 g of XPhos Pd G3.

Custom Q&A

What are some synonyms for XPhos Pd G3?

Methanesulfonato(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)

What is the molecular formula of XPhos Pd G3?

C46H62NO3PPdS

What is the melting point of XPhos Pd G3?

146-151°C (decomposition)

How should XPhos Pd G3 be stored?

Under inert gas (nitrogen or Argon) at 2-8°C

What color is XPhos Pd G3?

White to off-white

What is the reaction for which XPhos Pd G3 can be used as a palladium precatalyst?

C-N cross-coupling reactions

What are some specific uses of XPhos Pd G3 in reactions?

Cyanation reaction of heterocyclic halides, coupling of heteroaryl chlorides with polyfluoroaryl zinc reagents, coupling of 2,6-difluorophenylboronic acid with (hetero)aryl chlorides

What are some characteristics of XPhos Pd G3 as a reagent for Suzuki cross-coupling reactions?

Lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species, and accurate control of ligand: palladium ratio

What is the general description of XPhos Pd G3 as a third generation Buchwald precatalyst?

Air, moisture, and thermally-stable, highly soluble in a wide range of common organic solvents, long life in solutions, and excellent for Suzuki cross-coupling reactions