1420041-40-2Relevant academic research and scientific papers
Stereoselective One-Pot Sequential Dehydrochlorination/trans-Hydrofluorination Reaction of β-Chloro-α,β-unsaturated Aldehydes or Ketones: Facile Access to (Z)-β-Fluoro-β-arylenals/β-Fluoro-β-arylenones
Zhang, Jingli,Liu, Liran,Duan, Junxin,Gu, Lianghu,Chen, Bifeng,Sun, Taolei,Gong, Yuefa
, p. 4348 - 4358 (2017)
The monofluoroalkene substructure shows a high potential as a fluorinated synthon in organic synthesis. However, control of the Z/E stereoselectivity of multi-substituted monofluoroalkene products in one-pot reactions still remains a challenge. An unprecedented one-pot approach for the highly regio- and stereoselective preparation of functionalized (Z)-β-monofluoro tri-substituted alkenes from readily available β-chloro-α,β-unsaturated aldehydes or ketones has been explored. Mechanistic studies demonstrated that the reaction is initiated by dehydrochlorination of the substrates to give alkynyl aldehydes/ketones, followed by their trans-hydrofluorination. It is worth mentioning that a fluorinating reagent with suitable basicity and nucleophilicity plays a key role in promoting the formation of (Z)-β-fluoro-β-aryl tri-substituted monofluoroalkenes. (Figure presented.).
Silver-assisted difunctionalization of terminal alkynes: Highly regio- and stereoselective synthesis of bromofluoroalkenes
Li, Yibiao,Liu, Xiaohang,Ma, Deyun,Liu, Bifu,Jiang, Huanfeng
supporting information, p. 2683 - 2688 (2013/01/15)
The difunctionalization of terminal alk- ACHTUNGTRENUNGynes was achieved with silver fluoride (AgF) and N-bromosuccinimide (NBS) as halogen sources. The presence of the halide moiety greatly enhances the reactivity of the vinyl fluoride compounds that can probably can be transformed into various products that are difficult or even impossible to obtain via direct fluorination. Meanwhile, the monofluoro alkenes were facilely synthesized via a highly chemo- and regioselective fluorination of electron-deficient C-C triple bonds using AgF as fluorinating reagent in good yields
