Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis
Publication type: Journal Article
Publication date: 2020-06-22
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
32227612
General Chemistry
Catalysis
Organic Chemistry
Abstract
This work reveals ambident nucleophilic reactivity of imidazolium cations towards carbonyl compounds at the C2 or C4 carbene centers depending on the steric properties of the substrates and reaction conditions. Such an adaptive behavior indicates the dynamic nature of organocatalysis proceeding via a covalent interaction of imidazolium carbenes with carbonyl substrates and can be explained by generation of the H-bonded ditopic carbanionic carbenes.
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11
Total citations:
11
Citations from 2025:
1
(9.09%)
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GOST
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Galkin K. I. et al. Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis // Chemistry - A European Journal. 2020. Vol. 26. No. 39. pp. 8567-8571.
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Galkin K. I., Karlinskii B. Ya., Kostyukovich A. Y., Gordeev E. I., Ananikov V. P. Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis // Chemistry - A European Journal. 2020. Vol. 26. No. 39. pp. 8567-8571.
Cite this
RIS
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TY - JOUR
DO - 10.1002/chem.201905704
UR - https://doi.org/10.1002/chem.201905704
TI - Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis
T2 - Chemistry - A European Journal
AU - Galkin, Konstantin I
AU - Karlinskii, Bogdan Ya
AU - Kostyukovich, Alexander Yu.
AU - Gordeev, Evgeniy I
AU - Ananikov, Valentine P.
PY - 2020
DA - 2020/06/22
PB - Wiley
SP - 8567-8571
IS - 39
VL - 26
PMID - 32227612
SN - 0947-6539
SN - 1521-3765
ER -
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BibTex (up to 50 authors)
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@article{2020_Galkin,
author = {Konstantin I Galkin and Bogdan Ya Karlinskii and Alexander Yu. Kostyukovich and Evgeniy I Gordeev and Valentine P. Ananikov},
title = {Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis},
journal = {Chemistry - A European Journal},
year = {2020},
volume = {26},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/chem.201905704},
number = {39},
pages = {8567--8571},
doi = {10.1002/chem.201905704}
}
Cite this
MLA
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Galkin, Konstantin I., et al. “Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis.” Chemistry - A European Journal, vol. 26, no. 39, Jun. 2020, pp. 8567-8571. https://doi.org/10.1002/chem.201905704.