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Synthetic Applications of Monofluoromethylsulfonium Salts
Synthesis ( IF 2.2 ) Pub Date : 2021-07-13 , DOI: 10.1055/a-1548-8240
Janis Veliks , Renate Melngaile

Monofluoromethylsulfonium salts are emerging reagents for the fluoromethylation and fluoromethylenation or fluoromethylene transfer. Using this type of reagent is a simple approach for the introduction of the fluoromethyl group into a wide range of nucleophiles using mild basic conditions. Recently, fluoromethylsulfonium salts have been demonstrated to act as a synthetic equivalent for the challenging fluoromethylene synthon. For instance, these reagents can be used for the direct synthesis of monofluoroepoxides and fluorocyclopropanes from activated alkenes via a sulfur fluoromethylide intermediate. Sulfonium salts are an alternative, easy-to-handle option to volatile and environmentally concerning freons for achieving monofluorinated compounds. This review focuses on synthetic application of these reagents known to date.1 Introduction2 Fluoromethylation of O-, N-, S-, P-, and C-Nucleophiles3 Sulfonium Salts for Radical Monofluoromethylation of Alkenes4 Sulfonium Salts for Fluoromethylene Transfer5 Conclusions

中文翻译:

单氟甲基锍盐的合成应用

单氟甲基锍盐是用于氟甲基化和氟甲基化或氟亚甲基转移的新兴试剂。使用这种类型的试剂是一种使用温和碱性条件将氟甲基引入各种亲核试剂的简单方法。最近,氟甲基锍盐已被证明可作为具有挑战性的氟亚甲基合成子的合成等效物。例如,这些试剂可用于通过硫氟甲基化物中间体从活化的烯烃直接合成单氟环氧化物和氟环丙烷。锍盐是一种替代的、易于处理的选择,可替代挥发性和环境相关的氟利昂,以实现单氟化化合物。本综述侧重于迄今为止已知的这些试剂的合成应用。
更新日期:2021-08-07
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