Bench-Stable Electrophilic Fluorinating Reagents for Highly Selective Mono- and Difluorination of Silyl Enol Ethers
| Autor: | Aikawa Kohsuke, Akiya Adachi, Kyoko Nozaki, Ishibashi Yuichiro, Takashi Okazoe |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification Silylation 010405 organic chemistry Organic Chemistry Substrate (chemistry) Stereoisomerism General Chemistry 010402 general chemistry Highly selective 01 natural sciences Enol Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Alcohols Electrophile Indicators and Reagents Acyl group Ethers |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 27(46) |
| ISSN: | 1521-3765 |
| Popis: | Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron-withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base-free conditions. Thus, both mono- and difluorinated target materials were prepared from the same substrate. |
| Databáze: | OpenAIRE |
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