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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Synthesis, Characterizations and Applications of Fluoroazaphosphatranes
Anne-Doriane Manick1, Jean-Pierre Dutasta2, Paola Nava1
1Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France.
Chemistry, an Asian Journal
|April 1, 2022
Summary
A new synthesis provides access to fluoroazaphosphatranes, robust organocatalysts for CO2 conversion. These compounds are more stable than their chloro-analogs, enabling efficient cyclic carbonate formation from epoxides and CO2.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Green Chemistry
Background:
- Haloazaphosphatranes are key precursors to Verkade's superbase.
- Previous synthesis of fluoroazaphosphatranes is limited and lacks versatility.
- A need exists for a general method to synthesize diverse fluoroazaphosphatranes.
Purpose of the Study:
- Develop a simple and versatile synthesis for fluoroazaphosphatranes.
- Investigate the stability and catalytic applications of fluoroazaphosphatranes.
- Explore their use in CO2 conversion into cyclic carbonates.
Main Methods:
- Nucleophilic substitution of chloroazaphosphatranes with fluoride anions.
- Synthesis of various substituted fluoroazaphosphatranes.
- X-ray crystallography for structural determination.
- Testing fluoroazaphosphatranes as organocatalysts for CO2 cycloaddition.
Main Results:
- Achieved good to high yields (70-92%) for fluoroazaphosphatranes.
- Successfully synthesized diverse fluoroazaphosphatranes with various substituents.
- Fluoroazaphosphatranes exhibit enhanced stability compared to chloro-analogs.
- Demonstrated efficient and stable organocatalysis for CO2 conversion into cyclic carbonates.
Conclusions:
- A novel, simple, and versatile synthetic route to fluoroazaphosphatranes has been established.
- Fluoroazaphosphatranes are robust and efficient catalysts for CO2 utilization.
- This work expands the utility of azaphosphatranes in sustainable chemistry.
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