Chloro[(tri-tert-butylphosphine)-2'-amino[1,1'-biphenyl]-2-yl]palladium(II)
[CAS# 1375325-71-5]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: Chloro[(tri-tert-butylphosphine)-2'-amino[1,1'-biphenyl]-2-yl]palladium(II)
• Molecular Formula: C₂₄H₃₇ClNPPd
• Molecular Weight: 512.40
• CAS Registry Number: 1375325-71-5
• EC Number: 805-791-3
• SMILES: CC(C)(C)P(C(C)(C)C)C(C)(C)C.c1ccc(c(c1)c2ccccc2[Pd]Cl)N

Properties

• Melting point: 167-170 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	4	H302
Flammable solids	Flam. Sol.	1	H228
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Chloro[(tri-tert-butylphosphine)-2'-amino[1,1'-biphenyl]-2-yl]palladium(II), commonly known as P(t-Bu)₃Pd G2, is a palladium-based composite catalyst with the molecular formula C₃₀H₄₄ClNPdP. The discovery of P(t-Bu)₃Pd G2 stems from the ongoing research in the late 20th century aimed at developing more efficient palladium catalysts. Palladium-catalyzed cross-coupling reactions are essential for the formation of carbon-carbon bonds, requiring catalysts that can operate with high selectivity and stability under mild conditions. The researchers designed P(t-Bu)₃Pd G2 by combining palladium with macromolecular phosphine and aminobiphenyl ligands, which improves stability and reactivity.

P(t-Bu)₃Pd G2 has a palladium center coordinated to a chlorine atom, a tri-tert-butylphosphine ligand, and an aminobiphenyl group. The steric bulk of the tert-butyl and biphenyl backbones provides stability and affects the performance of the catalyst.

P(t-Bu)₃ Pd G2 is widely used in palladium-catalyzed cross-coupling reactions, which are essential for organic synthesis. Using Suzuki-Miyaura coupling, it promotes the reaction between aryl halides and boronic acids to form biaryl compounds, which are important for pharmaceuticals and materials science. Using Negishi coupling, the catalyst couples organozinc compounds with aryl halides, providing a route to the synthesis of complex organic molecules. Using Buchwald-Hartwig amination, P(t-Bu)₃ Pd G2 forms carbon-nitrogen bonds for the synthesis of amines and anilines, which are very important in medicinal chemistry.

In pharmaceutical synthesis, P(t-Bu)₃ Pd G2 enables the efficient synthesis of complex drug molecules, including those with biaryl or heteroaryl structures. The catalyst is suitable for large-scale drug production due to its high activity and tolerance to a variety of functional groups, ensuring efficient production of drug candidates.

P(t-Bu)₃ Pd G2 plays an important role in the development of advanced materials. The catalyst is used to synthesize conjugated polymers, which can be used in electronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaics. It helps create materials with specific electronic and photonic properties, promoting the development of nanotechnology and materials engineering.

P(t-Bu)₃ Pd G2 is essential in the following studies. Researchers use it to study the mechanism of palladium-catalyzed reactions, thereby developing new and improved catalysts. The catalyst is used to develop new synthetic methods, enhancing the toolbox available for organic synthesis.

References

2020. Palladium-catalyzed cross-couplings by C-O bond activation. Catalysis Science & Technology, 10(18).
DOI: 10.1039/D0CY01159B

2018. Palladium-catalyzed primary amine-directed regioselective mono- and di-alkynylation of biaryl-2-amines. Chemical Communications, 54(14).
DOI: 10.1039/C7CC09308J