2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl
[CAS# 787618-22-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: 2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl
• Synonyms: RuPhos; dicyclohexyl-[2-[2,6-di(propan-2-yloxy)phenyl]phenyl]phosphane
• Molecular Formula: C₃₀H₄₃O₂P
• Molecular Weight: 466.63
• CAS Registry Number: 787618-22-8
• EC Number: 616-653-5
• SMILES: CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4

Properties

• Melting point: 123-126 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H413
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl, commonly referred to as DCyP-Diiso, is an advanced phosphine ligand with significant implications in the field of catalysis. This compound is known for its distinctive structure and its role in enhancing the efficiency of metal-catalyzed reactions.

The ligand is characterized by a biphenyl backbone with two isopropoxy groups located at the 2' and 6' positions. Attached to this backbone are two dicyclohexylphosphino groups. The combination of these components creates a ligand with notable steric and electronic properties, which are crucial for its effectiveness as a catalyst.

The discovery of DCyP-Diiso emerged from the ongoing need for improved ligands that can offer better control over catalytic reactions. The bulky dicyclohexylphosphino groups provide significant steric protection to the metal center, which helps stabilize the catalyst during reactions. This stabilization is essential for maintaining catalytic activity and preventing deactivation, leading to more efficient and reliable catalytic processes.

DCyP-Diiso is predominantly used in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura, Heck, and Negishi reactions. These reactions are fundamental in organic synthesis for forming carbon-carbon bonds, which are essential for constructing complex organic molecules. The presence of the isopropoxy groups enhances the electronic properties of the ligand, optimizing the palladium catalyst’s performance in these reactions. This optimization leads to improved yields and selectivity, particularly when working with challenging substrates.

The unique structure of DCyP-Diiso also makes it suitable for a variety of other catalytic processes, including carbonylation and C-H activation reactions. Its ability to stabilize the metal center while providing fine-tuning of the electronic environment makes it a versatile tool in synthetic chemistry.

The development of DCyP-Diiso highlights the advancements in ligand design aimed at improving catalytic performance. Its effectiveness in palladium-catalyzed reactions and other catalytic processes underscores its value in both academic research and industrial applications.

Overall, 2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl represents a significant contribution to the field of organometallic chemistry. Its distinctive features and applications in various catalytic processes exemplify the ongoing progress in designing ligands that enhance reaction efficiency and selectivity.

References

2024. Synthetic techniques for thermodynamically disfavoured substituted six-membered rings. Nature Reviews Chemistry, 8(5).
DOI: 10.1038/s41570-024-00612-3

2018. Retaining Alkyl Nucleophile Regiofidelity in Transition-Metal-Mediated Cross-Couplings to Aryl Electrophiles. Synthesis, 50(17).
DOI: 10.1055/s-0037-1609941

2019. Applications in the Synthesis of Medicinal and Natural Compounds. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-230-00257