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Air‐Stable Oxyallyl Patterns and a Switchable N‐Heterocyclic Carbene
Author(s) -
TomásMendivil Eder,
Devillard Marc,
Regnier Vianney,
Pecaut Jacques,
Martin David
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202002669
Subject(s) - mesoionic , carbene , moiety , pyrimidine , ligand (biochemistry) , chemistry , combinatorial chemistry , photochemistry , organic chemistry , stereochemistry , catalysis , biochemistry , receptor
Abstract Oxyallyl derivatives are typically elusive compounds. Even recently reported “stabilized” 1,3‐diaminooxyallyl species are still highly reactive and have short lifetimes at room temperature. Herein, we report the synthesis and preliminary study of mesoionic pyrimidine derivatives that feature 1,3‐bis(dimethylamino)oxyallyl patterns with an unprecedented level of stabilization. The latter are not only insensitive towards air and moisture, but they are also compatible with the formation of an ancillary stable N‐heterocyclic carbene moiety. As the oxyallyl pattern is proton‐responsive, it allows the reversible switching of the electronic properties of the carbene, as a ligand.