(SP-4-4)-[2'-Amino[1,1'-biphenyl]-2-yl]chloro[dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine]palladium
[CAS# 1310584-14-5]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: (SP-4-4)-[2'-Amino[1,1'-biphenyl]-2-yl]chloro[dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine]palladium
• Molecular Formula: C₄₅H₅₉ClNPPd
• Molecular Weight: 786.80
• CAS Registry Number: 1310584-14-5
• EC Number: 694-646-6
• SMILES: CC(C)c1cc(c(c(c1)C(C)C)c2cccc(c2)P(C3CCCCC3)C4CCCCC4)C(C)C.CC(C)c1cc(c(c(c1)C(C)C)c2ccccc2P(C3CCCCC3)C4CCCCC4)C(C)C.c1ccc(c(c1)c2ccccc2[Pd]Cl)N.c1ccc(c(c1)c2ccccc2[Pd]Cl)N

Properties

• Melting point: 202-210 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Flammable solids	Flam. Sol.	1	H228
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

(SP-4-4)-[2'-amino[1,1'-biphenyl]-2-yl]chloro[dicyclohexyl[2',4',6'-tri(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine]palladium, commonly known as XPhos Pd G2, is a second-generation palladium catalyst that is noteworthy for its efficiency in cross-coupling reactions. XPhos Pd G2 was developed to improve catalytic activity and stability and plays an important role in modern synthetic chemistry. XPhos Pd G2 is derived from the XPhos family of ligands, which include phosphine ligands known for their bulky and electron-rich properties. XPhos ligands were developed to address the limitations of traditional palladium catalysts by providing better reactivity and functional group tolerance. Specifically, XPhos Pd G2 combines a palladium center with a chlorinated ligand and a dicyclohexylphosphine ligand to form a robust catalyst with enhanced performance in a variety of coupling reactions.

The structure of XPhos Pd G2 features a palladium atom coordinated with a chloride ligand and a complex dicyclohexyl[2',4',6'-tri(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine ligand. This arrangement contributes to its high reactivity and stability. The steric bulk and electronic properties of the ligand enhance the catalyst's ability to activate a wide range of substrates, making it effective in challenging coupling reactions.

XPhos Pd G2 is widely used in Suzuki-Miyaura coupling reactions to promote carbon-carbon bond formation between aryl or vinyl halides and boronic acids. Its high reactivity and functional group compatibility make it a top choice for the synthesis of biaryl compounds, which are essential intermediates in pharmaceuticals and agrochemicals.

The catalyst is also effective in the Buchwald-Hartwig amination reaction, which forms a carbon-nitrogen bond between aryl halides and amines. The unique ligand environment of XPhos Pd G2 supports the activation of less active substrates, enabling the synthesis of complex amines and heterocycles for drug discovery and development.

XPhos Pd G2 functions in Negishi couplings, promoting reactions between organozinc compounds and organohalides. This coupling is valuable for building carbon-carbon bonds in the synthesis of natural products and advanced materials.

In addition to its role in cross-coupling reactions, XPhos Pd G2 is used in a variety of industries and research: its efficiency in coupling reactions makes XPhos Pd G2 an important tool in pharmaceutical synthesis, enabling the rapid assembly of complex drug molecules in high yield and selectivity.

XPhos Pd G2 is used to synthesize functional materials, including polymers and organic electronic components. Its ability to form precise bonds facilitates the development of advanced materials with tailored properties.

The catalyst is widely used in academic research to explore new chemical transformations and reaction mechanisms. Its versatility and effectiveness in a variety of coupling reactions provide a platform for the development of innovative synthetic methods.

References

2017. Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki-Miyaura coupling and iron-catalyzed reduction. Organic & Biomolecular Chemistry, 15(47).
DOI: 10.1039/C7OB02373A

2018. Room-temperature borylation and one-pot two-step borylation/Suzuki-Miyaura cross-coupling reaction of aryl chlorides. RSC Advances, 8(25).
DOI: 10.1039/C8RA01381K

2017. Efficient synthesis of benzene-fused 6/7-membered amides via Xphos Pd G2 catalyzed intramolecular C-N bond formation. Chemical Communications, 53(65).
DOI: 10.1039/C7RA09160E