63315-98-0Relevant academic research and scientific papers
Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines
Novikov, Maxim A.,Ibatov, Yaroslav A.,Volchkov, Nikolai V.,Lipkind, Maria B.,Semenov, Sergei E.,Nefedov, Oleg M.
, p. 58 - 72 (2017)
Ring-opening amination of gem-chlorofluoro- and gem-bromofluorocyclopropanes with secondary alkyl, aryl amines or hydroxylamines catalyzed by copper(I) or copper(II) compounds with no additional ligands affords tertiary 2-fluoroallylamines or hydroxylamines in moderate to excellent yields. The reaction pathway involves isomerization of gem-fluorohalocyclopropanes to 2-fluoroallyl halides followed by in situ nucleophilic substitution of a halide by an N-nucleophile. The p-methoxyphenyl (PMP) protective group is efficient in the preparation of secondary 2-fluoroallylamines by this method. Primary 2-fluoroallylamines can only be obtained by a stepwise protocol including CuX-catalyzed isomerization of gem-fluorohalocyclopropanes to 2-fluoroallylic halides followed by amination.
