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Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N‐Heterocyclic Carbene‐Mediated Organocatalysis
Author(s) -
Galkin Konstantin I.,
Karlinskii Bogdan Ya.,
Kostyukovich Alexander Yu.,
Gordeev Evgeniy G.,
Ananikov Valentine P.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905704
Subject(s) - carbene , organocatalysis , reactivity (psychology) , chemistry , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , medicine , alternative medicine , pathology
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.