[2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]bis(1,1-dimethylethyl)phosphine-κP](methanesulfonato-κO)-Palladium
[CAS# 1536473-72-9]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]bis(1,1-dimethylethyl)phosphine-κP](methanesulfonato-κO)-Palladium
• Synonyms: tBuBrettPhos Pd G3
• Molecular Formula: C₄₄H₆₂NO₅PPdS
• Molecular Weight: 854.43
• CAS Registry Number: 1536473-72-9
• EC Number: 812-231-1
• SMILES: CC(C)c1cc(c(c(c1)C(C)C)c2c(ccc(c2P(C(C)(C)C)C(C)(C)C)OC)OC)C(C)C.CS(=O)(=O)O[Pd]c1ccccc1c2ccccc2N

Properties

• Melting point: 119-131 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335-H412
• Precautionary Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovory and Applicatios

[2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]bis(1,1-dimethylethyl)phosphine-κP](methanesulfonato-κO)-palladium is an organometallic compound that has gained considerable attention for its catalytic applications in organic synthesis. This palladium complex is particularly valuable due to its ability to facilitate various carbon-carbon bond-forming reactions, which are essential in the synthesis of complex organic molecules used in pharmaceuticals, agrochemicals, and materials science.

The discovery of this compound is rooted in the continuous search for more efficient and selective palladium-based catalysts. Palladium has long been recognized for its versatility in catalysis, especially in cross-coupling reactions that form the backbone of modern synthetic organic chemistry. The development of new ligands that can enhance the reactivity, selectivity, and stability of palladium catalysts has led to the synthesis of highly specialized compounds like this one.

This palladium complex features a carefully designed coordination environment around the metal center. The palladium atom is coordinated to an amino-substituted biphenyl ligand, which stabilizes the metal center through both nitrogen (κN) and carbon (κC) atoms. This bidentate coordination is crucial for maintaining the structural integrity and reactivity of the catalyst. The complex is further stabilized by a phosphine ligand with bulky substituents: bis(1,1-dimethylethyl) groups attached to a 3,6-dimethoxy-2',4',6'-tris(1-methylethyl)biphenyl moiety. The steric bulk provided by these groups helps to control the approach of substrates to the palladium center, thereby enhancing the selectivity of the catalytic process.

One of the primary applications of this palladium complex is in the Suzuki-Miyaura cross-coupling reaction, a widely used method for forming biaryl compounds. These biaryl structures are prevalent in many pharmaceutical agents and advanced materials. The sterically demanding phosphine ligand in this complex plays a key role in minimizing side reactions and increasing the yield and purity of the desired products, which is particularly important in the synthesis of pharmaceuticals where high purity is required.

In addition to its role in the Suzuki-Miyaura reaction, this palladium complex is also effective in other palladium-catalyzed processes such as the Heck reaction and Buchwald-Hartwig amination. These reactions are indispensable for constructing complex molecular architectures, further demonstrating the versatility of this catalyst in organic synthesis.

The methanesulfonato (κO) group in this complex is another critical feature. This group not only enhances the solubility of the complex in various solvents but also contributes to the overall reactivity of the catalyst. The ability to function in a wide range of solvents makes this palladium complex highly adaptable to different reaction conditions, which is beneficial for both research and industrial applications.

In summary, [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[3,6-dimethoxy-2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]bis(1,1-dimethylethyl)phosphine-κP](methanesulfonato-κO)-palladium is a highly effective catalyst that plays a significant role in the advancement of organic synthesis. Its discovery and application highlight the importance of ligand design in enhancing the performance of palladium catalysts, making it an essential tool in the creation of complex organic molecules.

References

2023. Parallel multi-droplet platform for reaction kinetics and optimization. Chemical Science, 14(33).
DOI: 10.1039/D3SC02082G

2018. Selective modification of natural nucleophilic residues in peptides and proteins using arylpalladium complexes. Organic Chemistry Frontiers, 5(21).
DOI: 10.1039/C8QO00765A