2-(Diphenylphosphino)biphenyl
[CAS# 13885-09-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 2-(Diphenylphosphino)biphenyl
• Synonyms: diphenyl-(2-phenylphenyl)phosphane
• Molecular Formula: C₂₄H₁₉P
• Molecular Weight: 338.38
• CAS Registry Number: 13885-09-1
• EC Number: 808-087-4
• SMILES: C1=CC=C(C=C1)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

2-(Diphenylphosphino)biphenyl is a versatile compound in organophosphorus chemistry, known for its significance as a ligand in various catalytic applications. This chemical substance, often abbreviated as "dppb," features a biphenyl backbone with a diphenylphosphino group attached to one of its phenyl rings. Its unique structure and properties make it an important tool in organometallic chemistry.

The discovery of 2-(Diphenylphosphino)biphenyl can be traced back to research aimed at developing efficient ligands for metal-catalyzed reactions. The biphenyl structure provides a rigid, planar platform that contributes to the stability and reactivity of the ligand. The diphenylphosphino group, which acts as a donor for coordination with metal centers, enhances the ligand's ability to stabilize metal complexes and facilitate various chemical transformations.

One of the key applications of 2-(Diphenylphosphino)biphenyl is in catalytic processes, particularly in cross-coupling reactions. These reactions, which include Suzuki-Miyaura and Heck couplings, are crucial in the synthesis of complex organic molecules. The ligand's ability to form stable complexes with transition metals, such as palladium and nickel, makes it highly effective in promoting these reactions. For instance, in the Suzuki-Miyaura coupling, the ligand helps to achieve high yields and selectivities by coordinating with the palladium catalyst and facilitating the coupling of aryl or vinyl boronic acids with electrophiles.

In addition to cross-coupling reactions, 2-(Diphenylphosphino)biphenyl is also used in other catalytic applications, such as asymmetric hydrogenation and C-H activation. Its properties enable it to support a wide range of catalytic processes, making it a valuable tool for chemists working in both academic and industrial settings.

The ligand's effectiveness in these reactions can be attributed to its electronic and steric properties. The diphenylphosphino group provides strong donor ability, which helps stabilize metal centers and influence reaction pathways. The biphenyl backbone offers a rigid and well-defined structure that reduces the likelihood of side reactions and improves the overall efficiency of the catalytic process.

Moreover, the versatility of 2-(Diphenylphosphino)biphenyl extends beyond its use in traditional cross-coupling reactions. Its ability to form stable complexes with various metals allows it to be employed in the development of new catalytic methodologies and the exploration of novel reaction mechanisms.

In summary, 2-(Diphenylphosphino)biphenyl has established itself as an important ligand in organometallic chemistry. Its discovery has significantly contributed to advancements in catalytic chemistry, providing a valuable tool for a range of applications. The ligand's unique structural features and properties make it an essential component in the synthesis of complex organic molecules and the development of new catalytic processes.

References

2018. Syntheses, steric hindrance effects, luminescent properties and TD-DFT calculations for a series of copper(I) iodide coordination complexes. Transition Metal Chemistry.
DOI: 10.1007/s11243-018-0237-1

2020. Recent Advances in Triarylmethane Synthesis. Synthesis.
DOI: 10.1055/s-0040-1707115

2021. Rhodium-Catalyzed, Phosphorus(III)-Directed Hydroarylation of Internal Alkynes: Facile and Efficient Access to New Phosphine Ligands. Synlett.
DOI: 10.1055/a-1314-0064