Metal-free and Alkali-metal-catalyzed Synthesis of Isoureas from Alcohols and Carbodiimides

Arnaud Imberdis (1) , Guillaume Lefèvre (1) , Pierre Thuéry (1) , Thibault Cantat (1)

1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

The first addition of alcohols to carbodiimides catalyzed by transition metal-free compounds is reported, using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its alkali metal salts. Isoureas are obtained in short reaction times and high yields, using TBDK. Control of the coordination sphere of potassium with exogenous chelating ligands, combined with mechanistic DFT calculations, demonstrates the role and positive influence of the alkali cation on the kinetics.

Domains: Organic chemistry; Catalysis

Arnaud Imberdis, Guillaume Lefèvre, Pierre Thuéry, Thibault Cantat. Metal-free and Alkali-metal-catalyzed Synthesis of Isoureas from Alcohols and Carbodiimides. Angewandte Chemie, 2018, 130, pp.3138-3142. ⟨10.1002/ange.201711737⟩. ⟨cea-01700617⟩