163931-61-1 | Tetrabutylammonium difluorotriphenylsilicate(IV)

CAS:163931-61-1 | Tetrabutylammonium difluorotriphenylsilicate(IV) ,Description

Tetrabutylammonium difluorotriphenylsilicate(IV) (TBADFTPS) is a silicate salt which is used in laboratory experiments for a variety of purposes. It is an anion-exchange resin, which means it can be used to exchange anions from solutions. TBADFTPS has been used in a variety of scientific research applications, including chromatography, catalysis, and electrochemistry. Its unique properties make it a valuable tool for scientists and researchers.
 

Scientific Research Applications

• Nucleophilic Transfer and Stereoselectivity: Tetrabutylammonium difluorotriphenylsilicate (TBAT) functions as a fluoride source in the stereoselective nucleophilic transfer of CF3 to chiral N-(tert-butylsulfinyl)imines. This reaction achieves high yield and stereoselectivity with a range of sulfinylimines including aromatic, heterocyclic, and aliphatic types, suggesting an open transition state mechanism (Prakash, Mandal, & Olah, 2001).
• Fluorinating Agent and Stability: Tetrabutylammonium difluorotriphenylstannate, a variant of TBAT, acts as a fluorinating agent and is notable for its stability up to 210°C, being non-hygroscopic and not hydrated. It has been successfully used for enolsilylether alkylations with alkyl bromides, showing high efficiency even when exposed to moisture (Gingras, 1991).
• Nucleophilic Fluorinating Agent: As a nucleophilic fluorinating agent, tetrabutylammonium difluorotriphenylstannate has been prepared on a multigram scale and used both as a fluorinating agent and a synthetic equivalent to PhMgX or PhLi species. Its applications emphasize hypercoordination for improving selectivity, reactivity, and shelf-stability of reagents (Gingras, Chabre, & Raimundo, 2006).
• Silicon-Carbon Bond Cleavage: TBAT can serve as a fluoride source for cleaving silicon-carbon bonds. It facilitates the in situ generation of carbanions which couple with various electrophiles, including aldehydes and ketones. Its advantages over tetrabutylammonium fluoride (TBAF) include being anhydrous, nonhygroscopic, and less basic (Pilcher & DeShong, 1996).
• Catalysis in Organic Synthesis: It is used as a catalyst in organic synthesis. For example, it facilitates the production of difluoroenoxysilanes from acylsilanes and trifluoromethyltrimethylsilane, displaying a substantial catalytic effect compared to other fluoride sources (Brigaud, Doussot, & Portella, 1994).
• In Vinylsilane Cross-Coupling Reactions: Tetrabutylammonium bifluoride, a related compound, has been utilized as an activating agent in copper-catalyzed vinylsilane cross-coupling reactions, demonstrating its versatility in different nucleophilic environments (Cornelissen, Nagy, Leyssens, & Riant, 2017).

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