Development of N-F fluorinating agents and their fluorinations: Historical perspective
| Autor: | Yuhao Yang, Teruo Umemoto, Gerald B. Hammond |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Research areas Chemistry fluorosulfonimide Science Organic Chemistry chemistry.chemical_element Salt (chemistry) DABCO Optically active fluoropyridinium salt 010402 general chemistry 01 natural sciences fluorination 0104 chemical sciences fluorodiazoniabicyclo[2.2.2]octane salt chemistry.chemical_compound QD241-441 n-f fluorinating agent Reagent Fluorine Organic chemistry Octane |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 1752-1813 (2021) |
| ISSN: | 1860-5397 |
| Popis: | This review deals with the historical development of all N-F fluorinating agents developed so far. The unique properties of fluorine make fluorinated organic compounds attractive in many research areas and therefore fluorinating agents are important. N-F agents have proven useful by virtue of their easy handling. This reagent class includes many types of N-F compounds: perfluoro-N-fluoropiperidine, N-fluoro-2-pyridone, N-fluoro-N-alkylarenesulfonamides, N-fluoropyridinium salts and derivatives, N-fluoroquinuclidium salts, N-fluoro-trifluoromethanesulfonimide, N-fluoro-sultams, N-fluoro-benzothiazole dioxides, N-fluoro-lactams, N-fluoro-o-benzenedisulfonimide, N-fluoro-benzenesulfonimide, 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluoropyridinium-2-sulfonate derivatives, 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluorodinitroimidazole, N-fluoro-trichloro-1,3,5-triazinium salt, N-F ethano-Tröger’s base derivatives, N-fluoro-methanesulfonimide, N-fluoro-N-arylarenesulfonamides, bisN-F salts such as N,N’-difluorobipyridinium salts and N,N’-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts, and their many derivatives and analogs, including chiral N-F reagents such as optically active N-fluoro-sultam derivatives, N-fluoro-alkaloid derivatives, DABCO-based N-F derivatives, and N-F binaphthyldisulfonimides. The synthesis and reactions of these reagents are described chronologically and the review also discusses the relative fluorination power of each reagent and their mechanisms chronicling developments from a historical perspective. |
| Databáze: | OpenAIRE |
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