Angewandte Chemie - International Edition p. 11686 - 11690 (2015)
Update date:2022-08-03
Topics:
Guo, Wusheng
Gnzalez-Fabra, Joan
Bandeira, Nuno A. G.
Bo, Carles
Kleij, Arjan W.
The first chemo- and site-selective process for the formation of N-aryl-carbamates from cyclic organic carbonates and aromatic amines is reported. The reactions proceed smoothly under extremely mild reaction conditions using TBD (triazabicyclodecene) as an effective and cheap organocatalyst, thus providing a sustainable and new methodology for the formation of a wide variety of useful N-aryl carbamate synthons in good to excellent yields. Computational investigations have been performed and show the underlying reason for the observed unique reactivity as related to an effective proton-relay mechanism mediated by the bicyclic guanidine base. By relay: The previously unknown site-selective attack of arylamines on cyclic carbonates to deliver N-aryl carbamates as the principal product is reported. The organocatalyst TBD guides an effective proton-relay process, thus mediating a chemoselective formation of the carbamate target under extremely mild reaction conditions. The new methodology represents a sustainable, cheap, and attractive process towards these important N-aryl carbamate synthons.
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