Mechanochemical 1,1′-Carbonyldiimidazole-Mediated Synthesis of Carbamates

Marialucia Lanzillotto (1) , Laure Konnert (1) , Frédéric Lamaty (1) , Jean Martinez (1) , Evelina Colacino (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

1,1′-Carbonyldiimidazole (CDI) was used as an eco-friendly acylation agent for the mechanochemical preparation of carbamates. The anticonvulsant N-methyl-O-benzyl carbamate was obtained in a vibrational ball-mill, while planetary ball-mill was suitable to develop a new sustainable method to access N-protected amino esters with no racemization. Compared to the synthesis in solution, mechanochemistry proved to be a powerful tool enhancing the reactivity of both alcohol and carbamoyl-imidazole intermediate, under mild conditions, without the need of activation as usually reported for solution synthesis. This new technology provides a sustainable method for the synthesis of carbamates using 1,1′-carbonyldiimidazole.

Mots clés: Mechanochemistry; Carbamates; CDI; Carbonyldiimidazole; Amino esters; Protecting groups; Anticonvulsant; 1-1′-Carbonyldiimidazole

Domaines: Chimie organique

Marialucia Lanzillotto, Laure Konnert, Frédéric Lamaty, Jean Martinez, Evelina Colacino. Mechanochemical 1,1′-Carbonyldiimidazole-Mediated Synthesis of Carbamates. ACS Sustainable Chemistry & Engineering, 2015, 3 (11), pp.2882-2889. ⟨10.1021/acssuschemeng.5b00819⟩. ⟨hal-02370950⟩