Catalyst-free cycloaddition of 1,3-diene-1-carbamates with azodicarboxylates: A rapid click reaction

Thomas Varlet , Guillaume Levitre (1) , Pascal ́ Retailleau (1) , Géraldine Masson (1)

1 ICSN - Institut de Chimie des Substances Naturelles

Novel click reactions are of continued interest in many scientific research areas and applications. Herein, we report a novel practical, catalyst-free, azo-Diels-Alder reaction between dienecarbamates and azodicarboxylates exhibiting a remarkable functional group tolerance. The availability of starting materials, mild reaction conditions , chemoselectivity and scalability make this cycloaddition a viable supplement to the other reactions in "click" chemistry.

Domaines: Chimie; Chimie organique

Thomas Varlet, Guillaume Levitre, Pascal ́ Retailleau, Géraldine Masson. Catalyst-free cycloaddition of 1,3-diene-1-carbamates with azodicarboxylates: A rapid click reaction. Bioorganic and Medicinal Chemistry, 2019, 27 (12), pp.2438-2443. ⟨10.1016/j.bmc.2019.02.008⟩. ⟨hal-02324662⟩