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Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Brønsted Acids or Acidic Zeolites. / Nursahedova, Selbi K.; Ryabukhin, Dmitry S.; Muzalevskiy, Vasily M.; Iakovenko, Roman O.; Boyarskaya, Irina A.; Starova, Galina L.; Nenajdenko, Valentine G.; Vasilyev, Aleksander V.

в: European Journal of Organic Chemistry, Том 2019, № 6, 14.02.2019, стр. 1293-1300.

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

Harvard

Nursahedova, SK, Ryabukhin, DS, Muzalevskiy, VM, Iakovenko, RO, Boyarskaya, IA, Starova, GL, Nenajdenko, VG & Vasilyev, AV 2019, 'Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Brønsted Acids or Acidic Zeolites', European Journal of Organic Chemistry, Том. 2019, № 6, стр. 1293-1300. https://doi.org/10.1002/ejoc.201801645

APA

Nursahedova, S. K., Ryabukhin, D. S., Muzalevskiy, V. M., Iakovenko, R. O., Boyarskaya, I. A., Starova, G. L., Nenajdenko, V. G., & Vasilyev, A. V. (2019). Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Brønsted Acids or Acidic Zeolites. European Journal of Organic Chemistry, 2019(6), 1293-1300. https://doi.org/10.1002/ejoc.201801645

Vancouver

Nursahedova SK, Ryabukhin DS, Muzalevskiy VM, Iakovenko RO, Boyarskaya IA, Starova GL и пр. Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Brønsted Acids or Acidic Zeolites. European Journal of Organic Chemistry. 2019 Февр. 14;2019(6):1293-1300. https://doi.org/10.1002/ejoc.201801645

Author

Nursahedova, Selbi K. ; Ryabukhin, Dmitry S. ; Muzalevskiy, Vasily M. ; Iakovenko, Roman O. ; Boyarskaya, Irina A. ; Starova, Galina L. ; Nenajdenko, Valentine G. ; Vasilyev, Aleksander V. / Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Brønsted Acids or Acidic Zeolites. в: European Journal of Organic Chemistry. 2019 ; Том 2019, № 6. стр. 1293-1300.

BibTeX

@article{e80b4220237e44ae80d2dbd063614f1c,
title = "Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Br{\o}nsted Acids or Acidic Zeolites",
abstract = " The reaction of trifluoroacetyl alkynes [ArC≡C(C=O)CF 3 ] with H 2 SO 4 or TfOH affords products of addition of the acids to the acetylene bond. Hydrolysis of these adducts results in the formation of the corresponding 1,3-diketones existing in form of enols [Ar(HO)C=CH(C=O)CF 3 ] in up to 98 % yield. The application of less acidic TfOH-pyridine system permits transformation of these alkynes into the corresponding vinyl triflates in up to 76 % yield. Moreover, this reaction is totally stereoselective to give only Z-configured vinyl triflates. The reaction of trifluoroacetyl alkynes with arenes in TfOH or under the action of acidic HUSY zeolites CBV-720 gives rise to 1,3-diaryl-1-CF 3 -indenes in up to 81 % yield. Electronic characteristics of initial intermediate mono- and dicationic species derived from such alkynes in the highly acidic media were studied by DFT calculations. Plausible cationic reaction mechanism was proposed. ",
keywords = "Alkynes, Electrophilic addition, Aromatic substitution, Protonation, Trifluoromethyl group, KETONES, DERIVATIVES, YNONES",
author = "Nursahedova, {Selbi K.} and Ryabukhin, {Dmitry S.} and Muzalevskiy, {Vasily M.} and Iakovenko, {Roman O.} and Boyarskaya, {Irina A.} and Starova, {Galina L.} and Nenajdenko, {Valentine G.} and Vasilyev, {Aleksander V.}",
year = "2019",
month = feb,
day = "14",
doi = "10.1002/ejoc.201801645",
language = "English",
volume = "2019",
pages = "1293--1300",
journal = "Liebigs Annalen der Chemie",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "6",

}

RIS

TY - JOUR

T1 - Reactions of Trifluoroacetyl Alkynes Under Electrophilic Activation with Brønsted Acids or Acidic Zeolites

AU - Nursahedova, Selbi K.

AU - Ryabukhin, Dmitry S.

AU - Muzalevskiy, Vasily M.

AU - Iakovenko, Roman O.

AU - Boyarskaya, Irina A.

AU - Starova, Galina L.

AU - Nenajdenko, Valentine G.

AU - Vasilyev, Aleksander V.

PY - 2019/2/14

Y1 - 2019/2/14

N2 - The reaction of trifluoroacetyl alkynes [ArC≡C(C=O)CF 3 ] with H 2 SO 4 or TfOH affords products of addition of the acids to the acetylene bond. Hydrolysis of these adducts results in the formation of the corresponding 1,3-diketones existing in form of enols [Ar(HO)C=CH(C=O)CF 3 ] in up to 98 % yield. The application of less acidic TfOH-pyridine system permits transformation of these alkynes into the corresponding vinyl triflates in up to 76 % yield. Moreover, this reaction is totally stereoselective to give only Z-configured vinyl triflates. The reaction of trifluoroacetyl alkynes with arenes in TfOH or under the action of acidic HUSY zeolites CBV-720 gives rise to 1,3-diaryl-1-CF 3 -indenes in up to 81 % yield. Electronic characteristics of initial intermediate mono- and dicationic species derived from such alkynes in the highly acidic media were studied by DFT calculations. Plausible cationic reaction mechanism was proposed.

AB - The reaction of trifluoroacetyl alkynes [ArC≡C(C=O)CF 3 ] with H 2 SO 4 or TfOH affords products of addition of the acids to the acetylene bond. Hydrolysis of these adducts results in the formation of the corresponding 1,3-diketones existing in form of enols [Ar(HO)C=CH(C=O)CF 3 ] in up to 98 % yield. The application of less acidic TfOH-pyridine system permits transformation of these alkynes into the corresponding vinyl triflates in up to 76 % yield. Moreover, this reaction is totally stereoselective to give only Z-configured vinyl triflates. The reaction of trifluoroacetyl alkynes with arenes in TfOH or under the action of acidic HUSY zeolites CBV-720 gives rise to 1,3-diaryl-1-CF 3 -indenes in up to 81 % yield. Electronic characteristics of initial intermediate mono- and dicationic species derived from such alkynes in the highly acidic media were studied by DFT calculations. Plausible cationic reaction mechanism was proposed.

KW - Alkynes

KW - Electrophilic addition, Aromatic substitution

KW - Protonation

KW - Trifluoromethyl group

KW - KETONES

KW - DERIVATIVES

KW - YNONES

UR - http://www.scopus.com/inward/record.url?scp=85059933001&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201801645

DO - 10.1002/ejoc.201801645

M3 - Article

AN - SCOPUS:85059933001

VL - 2019

SP - 1293

EP - 1300

JO - Liebigs Annalen der Chemie

JF - Liebigs Annalen der Chemie

SN - 1434-193X

IS - 6

ER -

ID: 44001750