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.

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NF氟化剂及其氟化的发展：历史视角

本综述涉及迄今为止开发的所有N -F 氟化剂的历史发展。氟的独特性质使氟化有机化合物在许多研究领域都很有吸引力，因此氟化剂很重要。N- F 试剂因其易于处理而被证明是有用的。这种试剂类包括许多类型的Ñ -F化合物：全氟- Ñ -fluoropiperidine，Ñ氟-2-吡啶酮，Ñ氟- Ñ -alkylarenesulfonamides，Ñ -fluoropyridinium盐和衍生物，Ñ -fluoroquinuclidium盐，Ñ -氟三氟甲磺酰亚胺，N-氟-磺胺、N-氟-苯并噻唑二氧化物、N-氟-内酰胺、N-氟-邻-苯二磺酰亚胺、N-氟-苯磺酰亚胺、1-烷基-4-氟-1,4-二氮杂二环[2.2.2]辛烷盐、N-氟吡啶鎓-2-磺酸盐衍生物、1-氟-4-羟基-1,4-重氮二环[2.2.2]辛烷盐、N-氟二硝基咪唑、N-氟-三氯-1,3,5-三嗪鎓盐、N -F 乙醇-Tröger 碱衍生物、N-氟-甲磺酰亚胺、N-氟-N-芳基芳烃磺酰胺、双N - F盐，例如N，N' -二氟联吡啶鎓盐和N , N' -difluoro-1,4-diazoniabicyclo[2.2.2] 辛烷盐，以及它们的许多衍生物和类似物，包括手性N -F 试剂，例如旋光N -fluoro-sultam 衍生物，N-氟-生物碱衍生物、基于DABCO的N - F衍生物和N- F联萘二磺酰亚胺。这些试剂的合成和反应按时间顺序描述，评论还讨论了每种试剂的相对氟化能力及其从历史角度记录发展的机制。