2'-[(1,1-Dimethylethyl)phenylphosphino]-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine
[CAS# 1660153-91-2]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: 2'-[(1,1-Dimethylethyl)phenylphosphino]-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine
• Synonyms: 2-[2-[tert-butyl(phenyl)phosphanyl]phenyl]-1-N,1-N,3-N,3-N-tetramethylbenzene-1,3-diamine
• Molecular Formula: C₂₆H₃₃N₂P
• Molecular Weight: 404.53
• CAS Registry Number: 1660153-91-2
• SMILES: CC(C)(C)P(C1=CC=CC=C1)C2=CC=CC=C2C3=C(C=CC=C3N(C)C)N(C)C

Properties

• Solubility: Insoluble (1.3E^-3 g/L) (25 °C), Calc.^*
• Melting point: 112 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

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

Discovery and Applications

2'-[(1,1-Dimethylethyl)phenylphosphino]-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine is a versatile chiral ligand that has garnered significant attention in the field of asymmetric catalysis. This compound, often abbreviated as a phosphine ligand, is known for its effectiveness in promoting enantioselective reactions, making it valuable in various synthetic applications.

The discovery of this ligand was driven by the need for highly selective chiral ligands to facilitate asymmetric transformations. Researchers sought to develop ligands that could efficiently catalyze reactions while providing high levels of enantiomeric purity. The ligand incorporates a [1,1'-biphenyl]-2,6-diamine backbone with substituents that enhance its chiral recognition and stability.

The ligand's core structure features a biphenyl moiety, which contributes to its rigidity and planar geometry, essential for its role in asymmetric catalysis. The 1,1-dimethylethylphenylphosphino group attached to the biphenyl backbone is crucial for its interaction with metal centers. This bulky phosphine group stabilizes the metal-ligand complex and provides steric protection, which is essential for achieving high selectivity in catalytic processes.

One of the primary applications of 2'-[(1,1-Dimethylethyl)phenylphosphino]-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine is in asymmetric hydrogenation. In this reaction, the ligand forms a complex with transition metals such as rhodium or ruthenium, facilitating the hydrogenation of alkenes and ketones to produce chiral alcohols and amines with high enantiomeric excess. This application is particularly valuable in the pharmaceutical industry, where the production of chiral intermediates is crucial for the synthesis of various drugs.

The ligand is also employed in asymmetric allylic substitution reactions. These reactions involve the nucleophilic substitution of an allylic group, leading to the formation of new chiral centers. The ligand's ability to stabilize the metal catalyst and control the stereochemistry of the reaction allows for the synthesis of complex chiral molecules used in the production of fine chemicals and natural products.

Additionally, 2'-[(1,1-Dimethylethyl)phenylphosphino]-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine has shown utility in other asymmetric transformations, such as cycloaddition and cross-coupling reactions. The ligand's versatility in various catalytic processes underscores its importance in advancing synthetic chemistry and developing new methodologies.

In summary, 2'-[(1,1-Dimethylethyl)phenylphosphino]-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine represents a significant advancement in the design of chiral ligands for asymmetric catalysis. Its discovery has enabled more efficient and selective catalytic processes, particularly in the synthesis of chiral molecules for pharmaceuticals and fine chemicals. The ligand's unique structural features and broad applicability highlight its role in the ongoing development of asymmetric synthesis techniques.

References

2016. Synthesis of Amino-Carbasugars. Synfacts, 13(1), 0087.
DOI: 10.1055/s-0036-1589734