Sulfoxantphos
[CAS# 215792-51-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Sulfoxantphos
• Synonyms: 4,5-Bis(diphenylphosphino)-9,9-dimethyl-2,7-disulfoxanthene disodium salt; 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene-2,7-disulfonic acid disodium salt
• Molecular Formula: C₃₉H₃₀O₇P₂S₂Na₂
• Molecular Weight: 782.71
• CAS Registry Number: 215792-51-1
• SMILES: CC1(C2=C(C(=CC(=C2)S(=O)(=O)[O-])P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=C(C=C5P(C6=CC=CC=C6)C7=CC=CC=C7)S(=O)(=O)[O-])C.[Na+].[Na+]

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Sulfoxantphos, with its unique chemical structure, represents a notable advance in the field of organophosphorus chemistry. It is primarily recognized for its application as a chiral ligand in various catalytic processes, particularly in asymmetric synthesis.

The discovery of Sulfoxantphos emerged from the pursuit of effective chiral ligands that could enhance the selectivity and efficiency of catalytic reactions. The development of Sulfoxantphos can be traced back to efforts to create ligands that combine both steric and electronic effects to achieve high levels of enantioselectivity. Its structure features a sulfoxide group attached to a xantphos framework, which is a well-known ligand structure in organophosphorus chemistry. This combination provides Sulfoxantphos with distinctive properties that are advantageous for its role in catalysis.

Sulfoxantphos is widely used in asymmetric synthesis, where it serves as a chiral ligand for transition metal-catalyzed reactions. Its effectiveness is particularly notable in the asymmetric hydrogenation of olefins, a process crucial for the synthesis of optically active compounds. The presence of the sulfoxide group in Sulfoxantphos contributes to its ability to influence the chiral environment around the metal center, thereby enhancing the enantioselectivity of the reactions. This property makes Sulfoxantphos an invaluable tool for the preparation of enantiomerically pure compounds, which are essential in the pharmaceutical industry and in the development of fine chemicals.

In addition to asymmetric hydrogenation, Sulfoxantphos is used in other catalytic transformations, including asymmetric transfer hydrogenation and asymmetric allylic alkylation. The versatility of Sulfoxantphos in these reactions is attributed to its ability to form stable complexes with transition metals, which facilitate various catalytic processes. The ligand’s robust performance in these reactions underscores its significance in advancing the field of asymmetric synthesis and expanding the scope of catalytic methodologies.

Beyond its applications in catalysis, Sulfoxantphos also contributes to the understanding of ligand design and the principles governing chirality in coordination chemistry. Research into the properties and behavior of Sulfoxantphos aids in the development of new ligands with enhanced performance characteristics, thereby advancing the broader field of organophosphorus chemistry.

In summary, Sulfoxantphos represents a significant achievement in the development of chiral ligands for asymmetric synthesis. Its effectiveness in a range of catalytic processes highlights its importance in the preparation of enantiomerically pure compounds and in advancing the field of organophosphorus chemistry.

References

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