Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines
Maxim I. Novikov
1
,
Yaroslav A. Ibatov
2
,
Nikolai V Volchkov
3
,
Maria B Lipkind
3
,
Sergei E Semenov
2
,
Oleg M. Nefedov
3
2
Moscow Chemical Liceum 1303, Moscow South-Eastern Lyceum and Grammar School Complex, 4 Tamozhennyy pr-d, 111033 Moscow, Russian Federation
|
Publication type: Journal Article
Publication date: 2017-02-01
scimago Q3
wos Q3
SJR: 0.333
CiteScore: 3.7
Impact factor: 1.9
ISSN: 00221139, 18733328
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Environmental Chemistry
Abstract
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.
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Total citations:
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Citations from 2025:
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(7.69%)
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Novikov M. I. et al. Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines // Journal of Fluorine Chemistry. 2017. Vol. 194. pp. 58-72.
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Novikov M. I., Ibatov Y. A., Volchkov N. V., Lipkind M. B., Semenov S. E., Nefedov O. M. Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines // Journal of Fluorine Chemistry. 2017. Vol. 194. pp. 58-72.
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TY - JOUR
DO - 10.1016/j.jfluchem.2017.01.001
UR - https://doi.org/10.1016/j.jfluchem.2017.01.001
TI - Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines
T2 - Journal of Fluorine Chemistry
AU - Novikov, Maxim I.
AU - Ibatov, Yaroslav A.
AU - Volchkov, Nikolai V
AU - Lipkind, Maria B
AU - Semenov, Sergei E
AU - Nefedov, Oleg M.
PY - 2017
DA - 2017/02/01
PB - Elsevier
SP - 58-72
VL - 194
SN - 0022-1139
SN - 1873-3328
ER -
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@article{2017_Novikov,
author = {Maxim I. Novikov and Yaroslav A. Ibatov and Nikolai V Volchkov and Maria B Lipkind and Sergei E Semenov and Oleg M. Nefedov},
title = {Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines},
journal = {Journal of Fluorine Chemistry},
year = {2017},
volume = {194},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.jfluchem.2017.01.001},
pages = {58--72},
doi = {10.1016/j.jfluchem.2017.01.001}
}
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