Standard

Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones. / Iakovenko, Roman O.; Kazakova, Anna N.; Boyarskaya, Irina A.; Gurzhiy, Vladislav V.; Avdontceva, Margarita S.; Panikorovsky, Taras L.; Muzalevskiy, Vasiliy M.; Nenajdenko, Valentine G.; Vasilyev, Aleksander V.

In: European Journal of Organic Chemistry, Vol. 2017, No. 37, 10.10.2017, p. 5632-5643.

Research output: Contribution to journal › Article › peer-review

Harvard

Iakovenko, RO, Kazakova, AN, Boyarskaya, IA, Gurzhiy, VV, Avdontceva, MS, Panikorovsky, TL, Muzalevskiy, VM, Nenajdenko, VG & Vasilyev, AV 2017, 'Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones', European Journal of Organic Chemistry, vol. 2017, no. 37, pp. 5632-5643. https://doi.org/10.1002/ejoc.201701085

APA

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. (2017). Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones. European Journal of Organic Chemistry, 2017(37), 5632-5643. https://doi.org/10.1002/ejoc.201701085

Vancouver

Iakovenko RO, Kazakova AN, Boyarskaya IA, Gurzhiy VV, Avdontceva MS, Panikorovsky TL et al. Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones. European Journal of Organic Chemistry. 2017 Oct 10;2017(37):5632-5643. https://doi.org/10.1002/ejoc.201701085

Author

Iakovenko, Roman O. ; Kazakova, Anna N. ; Boyarskaya, Irina A. ; Gurzhiy, Vladislav V. ; Avdontceva, Margarita S. ; Panikorovsky, Taras L. ; Muzalevskiy, Vasiliy M. ; Nenajdenko, Valentine G. ; Vasilyev, Aleksander V. / Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 37. pp. 5632-5643.

BibTeX

@article{73d1ecc7e516435ba5c9d14b70ed4e83,
title = "Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones",
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.",
keywords = "Carbocations, Carbocycles, Cyclization, Fluorine, Superacidic systems",
author = "Iakovenko, {Roman O.} and Kazakova, {Anna N.} and Boyarskaya, {Irina A.} and Gurzhiy, {Vladislav V.} and Avdontceva, {Margarita S.} and Panikorovsky, {Taras L.} and Muzalevskiy, {Vasiliy M.} and Nenajdenko, {Valentine G.} and Vasilyev, {Aleksander V.}",
year = "2017",
month = oct,
day = "10",
doi = "10.1002/ejoc.201701085",
language = "English",
volume = "2017",
pages = "5632--5643",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "37",

}

RIS

TY - JOUR

T1 - Superacid-Promoted Synthesis of CF3-Indenes Using Brominated CF3-Enones

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, Vasiliy M.

AU - Nenajdenko, Valentine G.

AU - Vasilyev, Aleksander V.

PY - 2017/10/10

Y1 - 2017/10/10

N2 - 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.

AB - 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.

KW - Carbocations

KW - Carbocycles

KW - Cyclization

KW - Fluorine

KW - Superacidic systems

UR - http://www.scopus.com/inward/record.url?scp=85030756945&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201701085

DO - 10.1002/ejoc.201701085

M3 - Article

AN - SCOPUS:85030756945

VL - 2017

SP - 5632

EP - 5643

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 37

ER -

ID: 33239708