2-{2-[bis(4-methoxy-3,5-dimethylphenyl)phosphanyl]phenyl}cyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide (1/1/1)
[CAS# 849925-20-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: 2-{2-[bis(4-methoxy-3,5-dimethylphenyl)phosphanyl]phenyl}cyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide (1/1/1)
• Synonyms: (1R)-1-[(1S)-1-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-[bis(4-methoxy-3,5-dimethylphenyl)phosphino]phenyl]Ferrocene; [2-[5-[(1S)-1-bis[3,5-bis(trifluoromethyl)phenyl]phosphanylethyl]cyclopenta-1,3-dien-1-yl]phenyl]-bis(4-methoxy-3,5-dimethylphenyl)phosphane cyclopenta-1,3-diene iron(2+)
• Molecular Formula: C₅₂H₄₄F₁₂FeO₂P₂
• Molecular Weight: 1046.68
• CAS Registry Number: 849925-20-8
• SMILES: Cc1cc(cc(c1OC)C)P(c2ccccc2[C]3[CH][CH][CH][C]3[C@@H](C)P(c4cc(cc(c4)C(F)(F)F)C(F)(F)F)c5cc(cc(c5)C(F)(F)F)C(F)(F)F)c6cc(c(c(c6)C)OC)C.[CH]1[CH][CH][CH][CH]1.[Fe]

Discovory and Applicatios

2-{2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphanyl]phenyl}cyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide (1/1/1) is a sophisticated chemical compound with important applications in organometallic chemistry and catalysis. This compound features a cyclopentadienide ring system with a phosphine ligand, making it notable for its role in enhancing catalytic processes.

The compound was synthesized to address the need for advanced ligands in transition metal catalysis. Its structure includes a cyclopentadienide core, a common feature in organometallic chemistry due to its stabilizing effects on metal centers. The core is substituted with phosphine groups that carry 4-methoxy-3,5-dimethylphenyl moieties. These phosphine ligands play a critical role in the reactivity and selectivity of the compound in catalytic reactions.

The discovery of 2-{2-[bis(4-methoxy-3,5-dimethylphenyl)phosphanyl]phenyl}cyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide (1/1/1) was driven by the need for more effective ligands in metal-catalyzed reactions. The phosphine groups on the cyclopentadienide ring offer a unique electronic environment that enhances the reactivity of the associated metal center, making it valuable for various catalytic processes.

One of the key applications of this compound is in catalytic hydrogenation. Hydrogenation reactions, which involve the addition of hydrogen to unsaturated compounds, require highly selective ligands. The compound's phosphine groups stabilize transition metals and promote selective hydrogenation, making it useful in the production of chiral chemicals and pharmaceuticals. The compound’s ability to facilitate efficient and selective hydrogenation is a significant advantage in synthesizing complex molecules with high enantiomeric purity.

Another important application is in cross-coupling reactions. These reactions, essential for forming carbon-carbon bonds in organic synthesis, benefit from the enhanced activity provided by the phosphine ligands. The compound’s role in improving yields and selectivity in cross-coupling reactions is crucial for the synthesis of complex organic molecules used in materials science and medicinal chemistry.

The design of 2-{2-[bis(4-methoxy-3,5-dimethylphenyl)phosphanyl]phenyl}cyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide (1/1/1) also represents a significant advancement in ligand development. By modifying the substituents on the cyclopentadienide and phosphine groups, researchers can tailor the ligand's electronic and steric properties. This capability is vital for advancing organometallic chemistry and expanding the range of catalytic processes available to chemists.

In summary, 2-{2-[bis(4-methoxy-3,5-dimethylphenyl)phosphanyl]phenyl}cyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide (1/1/1) is a notable advancement in organometallic chemistry. Its unique structure and versatile applications underscore its importance in catalysis and organic synthesis.