Air-Stable Oxyallyl Patterns and a Switchable N-Heterocyclic Carbene

Eder Tomas-Mendivil (1) , Marc Devillard (2, 3) , Vianney Regnier (1) , Jacques Pécaut (4, 5) , David Martin (1)

1 DCM - Département de Chimie Moléculaire
2 ISCR - Institut des Sciences Chimiques de Rennes
3 DCM - CIRE - Département de Chimie Moléculaire - Chimie Inorganique Redox
4 CIBEST - Chimie Interface Biologie pour l’Environnement, la Santé et la Toxicologie
5 DIESE - Département Interfaces pour l'énergie, la Santé et l'Environnement

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.

Mots clés: metal complexes; oxyallyl species; stable carbenes; substituent effects

Domaines: Chimie

Eder Tomas-Mendivil, Marc Devillard, Vianney Regnier, Jacques Pécaut, David Martin. Air-Stable Oxyallyl Patterns and a Switchable N-Heterocyclic Carbene. Angewandte Chemie International Edition, 2020, 59 (28), pp.11516-11520. ⟨10.1002/anie.202002669⟩. ⟨hal-02797042⟩