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Electrophilic Activation of 1-Aryl-3-bromo-2,2-difluoropropan-1-ones by Triflic Acid in Reactions with Arenes. / Aleksandrova, Maiia I.; Ivanov, Alexander Yu; Dilman, Alexander D.; Vasilyev, Aleksander V.

в: European Journal of Organic Chemistry, Том 2019, № 34, 15.09.2019, стр. 5905-5911.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Aleksandrova, MI, Ivanov, AY, Dilman, AD & Vasilyev, AV 2019, 'Electrophilic Activation of 1-Aryl-3-bromo-2,2-difluoropropan-1-ones by Triflic Acid in Reactions with Arenes', European Journal of Organic Chemistry, Том. 2019, № 34, стр. 5905-5911. https://doi.org/10.1002/ejoc.201900975

APA

Aleksandrova, M. I., Ivanov, A. Y., Dilman, A. D., & Vasilyev, A. V. (2019). Electrophilic Activation of 1-Aryl-3-bromo-2,2-difluoropropan-1-ones by Triflic Acid in Reactions with Arenes. European Journal of Organic Chemistry, 2019(34), 5905-5911. https://doi.org/10.1002/ejoc.201900975

Vancouver

Aleksandrova MI, Ivanov AY, Dilman AD, Vasilyev AV. Electrophilic Activation of 1-Aryl-3-bromo-2,2-difluoropropan-1-ones by Triflic Acid in Reactions with Arenes. European Journal of Organic Chemistry. 2019 Сент. 15;2019(34):5905-5911. https://doi.org/10.1002/ejoc.201900975

Author

Aleksandrova, Maiia I. ; Ivanov, Alexander Yu ; Dilman, Alexander D. ; Vasilyev, Aleksander V. / Electrophilic Activation of 1-Aryl-3-bromo-2,2-difluoropropan-1-ones by Triflic Acid in Reactions with Arenes. в: European Journal of Organic Chemistry. 2019 ; Том 2019, № 34. стр. 5905-5911.

BibTeX

@article{a919aed04ac44a51bc7d35fdc7cce4be,
title = "Electrophilic Activation of 1-Aryl-3-bromo-2,2-difluoropropan-1-ones by Triflic Acid in Reactions with Arenes",
abstract = "The reactions of 1-aryl-3-bromo-2,2-difluoropropan-1-ones [Ar(CO)CF2CH2Br] with various arenes Ar′H in the superacid TfOH at room temperature for 1–7 h result in the formation of products of hydroarylation of the carbonyl group, 1,1-diaryl-3-bromo-2,2-difluoropropan-1-ols [ArAr′C(OH)CF2CH2Br], in yields up to 85 %. The reaction with benzene goes deeper and leads to 1-aryl-3-bromo-2,2-difluoro-1,1-diphenylpropanes [ArCPh2CF2CH2Br] in good yields. Mainly, the bromomethyl group (CH2Br) of starting ketones remains untouched under the superacidic conditions. Cationic intermediates of the reaction have been studied by means of NMR spectroscopy. Plausible reaction mechanism is discussed.",
keywords = "Aromatic substitution, Difluoroalcohols, Difluoroketones, Protonation, Triflic acid",
author = "Aleksandrova, {Maiia I.} and Ivanov, {Alexander Yu} and Dilman, {Alexander D.} and Vasilyev, {Aleksander V.}",
year = "2019",
month = sep,
day = "15",
doi = "10.1002/ejoc.201900975",
language = "English",
volume = "2019",
pages = "5905--5911",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "34",

}

RIS

TY - JOUR

T1 - Electrophilic Activation of 1-Aryl-3-bromo-2,2-difluoropropan-1-ones by Triflic Acid in Reactions with Arenes

AU - Aleksandrova, Maiia I.

AU - Ivanov, Alexander Yu

AU - Dilman, Alexander D.

AU - Vasilyev, Aleksander V.

PY - 2019/9/15

Y1 - 2019/9/15

N2 - The reactions of 1-aryl-3-bromo-2,2-difluoropropan-1-ones [Ar(CO)CF2CH2Br] with various arenes Ar′H in the superacid TfOH at room temperature for 1–7 h result in the formation of products of hydroarylation of the carbonyl group, 1,1-diaryl-3-bromo-2,2-difluoropropan-1-ols [ArAr′C(OH)CF2CH2Br], in yields up to 85 %. The reaction with benzene goes deeper and leads to 1-aryl-3-bromo-2,2-difluoro-1,1-diphenylpropanes [ArCPh2CF2CH2Br] in good yields. Mainly, the bromomethyl group (CH2Br) of starting ketones remains untouched under the superacidic conditions. Cationic intermediates of the reaction have been studied by means of NMR spectroscopy. Plausible reaction mechanism is discussed.

AB - The reactions of 1-aryl-3-bromo-2,2-difluoropropan-1-ones [Ar(CO)CF2CH2Br] with various arenes Ar′H in the superacid TfOH at room temperature for 1–7 h result in the formation of products of hydroarylation of the carbonyl group, 1,1-diaryl-3-bromo-2,2-difluoropropan-1-ols [ArAr′C(OH)CF2CH2Br], in yields up to 85 %. The reaction with benzene goes deeper and leads to 1-aryl-3-bromo-2,2-difluoro-1,1-diphenylpropanes [ArCPh2CF2CH2Br] in good yields. Mainly, the bromomethyl group (CH2Br) of starting ketones remains untouched under the superacidic conditions. Cationic intermediates of the reaction have been studied by means of NMR spectroscopy. Plausible reaction mechanism is discussed.

KW - Aromatic substitution

KW - Difluoroalcohols

KW - Difluoroketones

KW - Protonation

KW - Triflic acid

UR - http://www.scopus.com/inward/record.url?scp=85071603353&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/electrophilic-activation-1aryl3bromo22difluoropropan1ones-triflic-acid-reactions-arenes

U2 - 10.1002/ejoc.201900975

DO - 10.1002/ejoc.201900975

M3 - Article

AN - SCOPUS:85071603353

VL - 2019

SP - 5905

EP - 5911

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 34

ER -

ID: 49830567