N-Vinyl-2-(trifluoroacetylethynyl)pyrroles and E-2-(1-bromo-2-trifluoroacetylethenyl)pyrroles: Cross-coupling vs. addition during C H-functionalization of pyrroles with bromotrifluoroacetylacetylene in solid Al2O3 medium. H-bonding control
Denis N. Tomilin
1
,
Maxim D Gotsko
1
,
Lyubov N. Sobenina
1
,
Igor Ushakov
1
,
A.V. Afonin
1
,
Dmitri Yu Soshnikov
2, 3
,
A.B. Trofimov
2, 3
,
Andrey B Koldobsky
4
,
Publication type: Journal Article
Publication date: 2016-06-01
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
A topochemical reaction of pyrroles with bromotrifluoroacetylacetylene proceeds in solid Al2O3 at room temperature in two different directions depending on the substituent character at the nitrogen atom. While N-vinylpyrroles undergo the cross-coupling to give N-vinyl-2-(trifluoroacetylethynyl)pyrroles in up to 58% yield, unsubstituted NH-pyrroles add to the triple bond to afford exclusively E-2-(1-bromo-2-trifluoroacetylethenyl)pyrroles in 12–21% yields. It has been shown (1H NMR, quantum-chemical calculations) that the reaction is controlled by the strong intramolecular hydrogen bonding between NH and carbonyl groups.
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Tomilin D. N. et al. N-Vinyl-2-(trifluoroacetylethynyl)pyrroles and E-2-(1-bromo-2-trifluoroacetylethenyl)pyrroles: Cross-coupling vs. addition during C H-functionalization of pyrroles with bromotrifluoroacetylacetylene in solid Al2O3 medium. H-bonding control // Journal of Fluorine Chemistry. 2016. Vol. 186. pp. 1-6.
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Tomilin D. N., Gotsko M. D., Sobenina L. N., Ushakov I., Afonin A., Soshnikov D. Yu., Trofimov A., Koldobsky A. B., Trofimov B. A. N-Vinyl-2-(trifluoroacetylethynyl)pyrroles and E-2-(1-bromo-2-trifluoroacetylethenyl)pyrroles: Cross-coupling vs. addition during C H-functionalization of pyrroles with bromotrifluoroacetylacetylene in solid Al2O3 medium. H-bonding control // Journal of Fluorine Chemistry. 2016. Vol. 186. pp. 1-6.
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TY - JOUR
DO - 10.1016/j.jfluchem.2016.03.012
UR - https://doi.org/10.1016/j.jfluchem.2016.03.012
TI - N-Vinyl-2-(trifluoroacetylethynyl)pyrroles and E-2-(1-bromo-2-trifluoroacetylethenyl)pyrroles: Cross-coupling vs. addition during C H-functionalization of pyrroles with bromotrifluoroacetylacetylene in solid Al2O3 medium. H-bonding control
T2 - Journal of Fluorine Chemistry
AU - Tomilin, Denis N.
AU - Gotsko, Maxim D
AU - Sobenina, Lyubov N.
AU - Ushakov, Igor
AU - Afonin, A.V.
AU - Soshnikov, Dmitri Yu
AU - Trofimov, A.B.
AU - Koldobsky, Andrey B
AU - Trofimov, B. A.
PY - 2016
DA - 2016/06/01
PB - Elsevier
SP - 1-6
VL - 186
SN - 0022-1139
SN - 1873-3328
ER -
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@article{2016_Tomilin,
author = {Denis N. Tomilin and Maxim D Gotsko and Lyubov N. Sobenina and Igor Ushakov and A.V. Afonin and Dmitri Yu Soshnikov and A.B. Trofimov and Andrey B Koldobsky and B. A. Trofimov},
title = {N-Vinyl-2-(trifluoroacetylethynyl)pyrroles and E-2-(1-bromo-2-trifluoroacetylethenyl)pyrroles: Cross-coupling vs. addition during C H-functionalization of pyrroles with bromotrifluoroacetylacetylene in solid Al2O3 medium. H-bonding control},
journal = {Journal of Fluorine Chemistry},
year = {2016},
volume = {186},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.jfluchem.2016.03.012},
pages = {1--6},
doi = {10.1016/j.jfluchem.2016.03.012}
}
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