TMSCFX2(X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes
TMSCFX2 (X = Cl, Br; TMS = trimethylsilyl) have been developed as halofluorocarbene (CFX, X = Cl, Br) precursors for [2+1] cyclopropanation with alkenes. Structurally diverse halofluorocyclopropanes were obtained in good to excellent yields. It was found
(NHC)AgCl catalyzed bromofluorocyclopropanation of alkenes with CFBr2CO2Na
An effective method for bromofluorocyclopropanation of electron-rich (aryl substituted), electron-neutral (monoalkyl substituted), electron-poor (haloalkenes, allylic esters, α,β-unsaturated esters) and acid/base sensitive silyl- and boronyl substituted a
Andrianova, Anastasia A.,Maslova, Yulia D.,Novikov, Maxim A.,Semenov, Sergei E.,Nefedov, Oleg M.
p. 49 - 55
(2018/03/08)
Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines
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.
Novikov, Maxim A.,Ibatov, Yaroslav A.,Volchkov, Nikolai V.,Lipkind, Maria B.,Semenov, Sergei E.,Nefedov, Oleg M.
supporting information
p. 58 - 72
(2017/01/18)
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