DavePhos-Pd-G3
[CAS# 1445085-87-9]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: DavePhos-Pd-G3
• Synonyms: 2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline;methanesulfonic acid;palladium;2-phenylaniline
• Molecular Formula: C₃₉H₅₀N₂O₃PPdS^-
• Molecular Weight: 764.28
• CAS Registry Number: 1445085-87-9
• EC Number: 811-488-7
• SMILES: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CS(=O)(=O)O.C1=CC=C([C-]=C1)C2=CC=CC=C2N.[Pd]

Properties

• Melting point: 183-200 ºC (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H351
• Precautionary Statements: P201-P202-P280-P308+P313-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	H351

Discovory and Applicatios

DavePhos-Pd-G3 is a specialized chemical substance combining a well-defined phosphine ligand with a palladium catalyst, playing a significant role in modern organic synthesis. This compound is part of the broader class of phosphine-palladium complexes, which are known for their utility in facilitating a range of chemical reactions, particularly in catalysis.

DavePhos-Pd-G3 consists of a palladium center coordinated with a DavePhos ligand, which is a phosphine ligand featuring a specific steric and electronic environment designed to optimize catalytic activity. The "G3" designation indicates a particular generation or variation of the DavePhos ligand, reflecting refinements made to enhance its performance.

The discovery of DavePhos-Pd-G3 is rooted in the ongoing effort to improve catalytic systems for complex organic transformations. Researchers sought to develop a palladium complex with enhanced reactivity and selectivity for various reactions, such as cross-coupling processes. The choice of the DavePhos ligand, known for its robust coordination properties and ability to stabilize palladium in various oxidation states, was critical in achieving these goals.

In applications, DavePhos-Pd-G3 is primarily used in cross-coupling reactions, such as the Suzuki-Miyaura and Buchwald-Hartwig couplings. These reactions are vital in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and materials. DavePhos-Pd-G3 excels in these processes due to the optimal electronic and steric properties imparted by the DavePhos ligand, which improves the efficiency and selectivity of the palladium catalyst.

The effectiveness of DavePhos-Pd-G3 in these reactions stems from the precise tuning of the phosphine ligand, which affects the palladium center's electronic characteristics and its interaction with substrates. This optimization leads to higher reaction rates, improved yields, and greater control over the reaction outcomes. Consequently, DavePhos-Pd-G3 has become a valuable tool for chemists engaged in both academic research and industrial applications.

Moreover, DavePhos-Pd-G3 has been explored for use in other catalytic transformations beyond cross-coupling reactions. Its versatility in various catalytic processes highlights its importance in developing new synthetic routes and enhancing existing methodologies.

Overall, DavePhos-Pd-G3 represents a significant advancement in the field of catalytic chemistry, offering improved performance in key organic reactions. Its development exemplifies the ongoing progress in designing catalysts with tailored properties to meet the demands of modern chemical synthesis.