Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones
Publication type: Journal Article
Publication date: 2017-10-09
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The reactions of 3-bromo- and 3,4-dibromo-CF3-enones with superacids were studied. Protonation of these CF3-enones with FSO3H resulted in the formation of cationic species that subsequently cyclized at –60 °C to give the corresponding mono- and dibromoindenols in up to 98 % yield. Protonation of the indenol products at room temperature with triflic acid (CF3SO3H) provided highly electrophilic trifluoromethylated indenyl cations. Subsequent reaction with various arenes gave access to 1-CF3-substituted indenes in up to 84 % yields. DFT calculations were carried out to obtain data about the electronic structure and electrophilicity of the cationic intermediates. The mechanisms of these multistep transformations of highly electrophilic cationic intermediates are discussed.
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28
Total citations:
28
Citations from 2024:
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(10.71%)
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GOST
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Iakovenko R. O. et al. Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 37. pp. 5632-5643.
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Iakovenko R. O., Kazakova A. N., Boyarskaya I. A., Gurzhiy V. V., Avdontceva M. S., Panikorovsky T. L., Muzalevskiy V. M., Nenajdenko V. G., Vasilyev A. V. Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones // European Journal of Organic Chemistry. 2017. Vol. 2017. No. 37. pp. 5632-5643.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.201701085
UR - https://doi.org/10.1002/ejoc.201701085
TI - Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones
T2 - European Journal of Organic Chemistry
AU - Iakovenko, Roman O
AU - Kazakova, Anna N
AU - Boyarskaya, Irina A
AU - Gurzhiy, Vladislav V.
AU - Avdontceva, Margarita S.
AU - Panikorovsky, Taras L
AU - Muzalevskiy, Vasily M.
AU - Nenajdenko, Valentine G.
AU - Vasilyev, Aleksander V
PY - 2017
DA - 2017/10/09
PB - Wiley
SP - 5632-5643
IS - 37
VL - 2017
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2017_Iakovenko,
author = {Roman O Iakovenko and Anna N Kazakova and Irina A Boyarskaya and Vladislav V. Gurzhiy and Margarita S. Avdontceva and Taras L Panikorovsky and Vasily M. Muzalevskiy and Valentine G. Nenajdenko and Aleksander V Vasilyev},
title = {Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones},
journal = {European Journal of Organic Chemistry},
year = {2017},
volume = {2017},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/ejoc.201701085},
number = {37},
pages = {5632--5643},
doi = {10.1002/ejoc.201701085}
}
Cite this
MLA
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Iakovenko, Roman O., et al. “Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones.” European Journal of Organic Chemistry, vol. 2017, no. 37, Oct. 2017, pp. 5632-5643. https://doi.org/10.1002/ejoc.201701085.
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