[2'-(Amino)[1,1'-biphenyl]-2-yl][bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium
[CAS# 1447963-75-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: [2'-(Amino)[1,1'-biphenyl]-2-yl][bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium
• Synonyms: Tbuxphos PD G3
• Molecular Formula: C₄₂H₅₈NO₃PPdS
• Molecular Weight: 794.37
• CAS Registry Number: 1447963-75-8
• EC Number: 811-771-5
• SMILES: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.CS(=O)(=O)O.C1=CC=C([C-]=C1)C2=CC=CC=C2N.[Pd]

Properties

• Melting point: 130-140 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335-H412
• Precautionary Statements: P261-P264-P270-P271-P273-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

[2'-(Amino)[1,1'-biphenyl]-2-yl][bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium is a highly specialized palladium complex that has garnered significant attention in the field of catalysis. This compound is particularly notable for its application in facilitating carbon-carbon bond formation, which is crucial in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and materials for electronic devices.

The discovery of this palladium complex is part of the broader effort to enhance the efficiency and selectivity of palladium-catalyzed reactions. Palladium catalysts are indispensable in modern organic chemistry due to their ability to promote a variety of bond-forming reactions under mild conditions. The development of new ligands that can fine-tune the reactivity and selectivity of palladium complexes is a key focus in this area of research, leading to the creation of complex structures like [2'-(Amino)[1,1'-biphenyl]-2-yl][bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium.

This compound features a palladium center coordinated with a biphenyl-based amine ligand and a bulky phosphine ligand. The biphenyl amine ligand provides electronic stabilization to the palladium atom, enhancing the overall reactivity of the complex. The phosphine ligand, characterized by its bis(1,1-dimethylethyl) and 2',4',6'-tris(1-methylethyl) substituents, introduces significant steric bulk. This bulkiness is crucial for controlling the catalytic environment around the palladium center, thereby increasing the selectivity of the catalytic process.

One of the most important applications of this palladium complex is in the Suzuki-Miyaura cross-coupling reaction. This reaction is widely used for constructing biaryl structures, which are key components in many pharmaceuticals and advanced materials. The bulky nature of the phosphine ligand in this complex helps to minimize side reactions and maximize the yield of the desired product. This is particularly valuable in pharmaceutical synthesis, where the purity and yield of the product are critical factors.

In addition to the Suzuki-Miyaura reaction, this complex is also used in other palladium-catalyzed processes such as the Heck reaction and Buchwald-Hartwig amination. These reactions are essential tools for building complex organic molecules, making this palladium complex a versatile catalyst in organic synthesis.

The methanesulfonato group in the complex plays a significant role in its solubility and reactivity. This group enhances the solubility of the complex in various solvents, allowing it to be used in a wide range of reaction conditions. This versatility makes the complex suitable for use in both academic research and industrial applications, where different solvents and conditions are often required.

In summary, [2'-(Amino)[1,1'-biphenyl]-2-yl][bis(1,1-dimethylethyl)[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonato)palladium is a highly effective and versatile catalyst that has made significant contributions to the field of organic synthesis. Its discovery and application underscore the importance of ligand design in enhancing the performance of palladium catalysts, making it an invaluable tool in modern chemistry.

References

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

2022. Pd/Cu bimetallic catalysis to access highly fluorinated biaryls from aryl halides and fluorinated arenes. Chemical Communications, 58(17).
DOI: 10.1039/D2CC00141A

2016. Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods. Chemical Science, 7(8).
DOI: 10.1039/C5SC04751J