889362-54-3Relevant academic research and scientific papers
Methyl NFSI: Atom-economical alternative to NFSI shows higher fluorination reactivity under Lewis acid-catalysis and non-catalysis
Fukushi, Kazunobu,Suzuki, Satoru,Kamo, Tomohiro,Tokunaga, Etsuko,Sumii, Yuji,Kagawa, Takumi,Kawada, Kosuke,Shibata, Norio
supporting information, p. 1864 - 1868 (2016/04/19)
Me-NFSI was first reported in 1994. Despite its atom-economical structure and similarity to a well-explored fluorinating reagent, NFSI, Me-NFSI has not appeared in the literature in over 20 years. We disclose that Me-NFSI is more effective for the fluorination of active methines under Lewis acid-catalysis and non-catalysis than NFSI.
Acetyl Hypofluorite, a New Moderating Carrier of Elemental Fluorine and Its Use in Fluorination of 1,3-Dicarbonyl Derivatives
Lerman, Ori,Rozen, Shlomo
, p. 724 - 727 (2007/10/02)
Elemental fluorine and most of the fluoroxy reagents do not react efficiently or cleanly with 1,3-dicarbonyl derivatives or with their corresponding metal enolates even at -75 degC.It has been found that a suspension of sodium acetate in CFCl3 or in CFCl3-AcOH, when treated with elemental fluorine, forms a new electrophilic fluorinating reagent, CH3COOF (1), which reacts with substrates without further isolation or purification.This reagent is milder than F2, CF3OF, or CF3COOF and reacts successfully where the other reagents fail.When 1 reacts with 1,3-dicarbonyl compounds, the main product is the 1,3-dioxo-2-fluoro derivative in reasonable yields.When, however, the corresponding sodium enolates were treated with 1, the yields of the monofluoro derivatives were considerably higher.In the case of 1,3-dicarbonyl derivatives with low enol content, only the sodium enolates react with 1 to produce good to very good yields of the corresponding 2-monofluoro derivatives.Thus 1 can be considered as a moderating carrier of the highly reactive F2.
