120801-75-4 | Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate

CAS:120801-75-4 | Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate ,Description

Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TMS-DFFA) is an organofluorine compound that has been used in a variety of scientific research applications. It is a versatile reagent that has been used in multiple synthetic and analytical processes. It is a stable compound with a wide range of applications, from organic synthesis and analytical chemistry to biochemistry and physiology.
 

Scientific Research Applications

• Catalysis in Acylation Reactions: Trimethylsilyl trifluoromethanesulfonate is effective in catalyzing the acylation of alcohols with acid anhydrides, providing a clean, efficient, and faster reaction compared to standard conditions (Procopiou, Baugh, Flack, & Inglis, 1998).
• Chemoselective Reactions: It also promotes chemoselective reactions of acyclic acetals with various reagents, demonstrating its versatility in organic synthesis (Kim, Do, Kim, & Kim, 1994).
• Diastereoselective Synthesis: The compound is used in the diastereoselective synthesis of β-amino esters and potentially trans-β-lactams, showcasing its application in stereocontrolled synthesis (Guanti, Narisano, & Banfi, 1987).
• Organofluorine Synthesis: It has been applied in the organocatalytic difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds, a method valuable for pharmaceutical and agrochemical synthesis (Fuchibe, Bando, Takayama, & Ichikawa, 2015).
• Precursors in Organic Synthesis: Trimethylsilyl esters, including derivatives of Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate, are used as precursors in various organic syntheses, such as in the preparation of difluoroaze derivatives (Bordeau, Frébault, Gobet, & Picard, 2006).
• Synthesis of Fluorosulfonyl Esters: Silver (fluorosulfonyl)difluoroacetate is used for synthesizing fluorosulfonyl esters, which have potential applications in pharmaceuticals and cosmetics (Terjeson, Mohtasham, Peyton, & Gard, 1989).
• Synthesis of Homoallyl Alcohols: It is utilized in coupling reactions with carbonyl compounds, leading to efficient access to 2,2-difluoro homoallyl alcohols (Ishihara, Miwatashi, Kuroboshi, & Utimoto, 1991).
• Thermolysis Studies: Studies on the thermolysis of trimethylsilyl esters provide insights into their decomposition and the products formed, which is significant in understanding their stability and reactivity (Werstiuk, Brook, & Hülser, 1988).
• Generation of Difluorocarbenes: It has been demonstrated to facilitate the generation of difluorocarbenes, used in synthesizing valuable organofluorine compounds including difluoromethyl (thio)ethers and fluorinated thiophenes (Fuchibe & Ichikawa, 2023).
• Synthesis of N-Vinyl Derivatives: The compound serves as a flexible catalyst in the synthesis of N-vinyl derivatives of nucleobases, indicating its utility in nucleoside chemistry (Dalpozzo et al., 2004).

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