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

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.
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Submitted on : Monday, September 28, 2020 - 12:08:37 PM
Last modification on : Wednesday, September 30, 2020 - 3:22:57 AM

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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, Wiley-VCH Verlag, 2020, 59 (28), pp.11516-11520. ⟨10.1002/anie.202002669⟩. ⟨hal-02797042⟩

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