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Wiley, Angewandte Chemie International Edition, 40(54), p. 11686-11690, 2015

DOI: 10.1002/anie.201504956

Wiley, Angewandte Chemie, 40(127), p. 11852-11856, 2015

DOI: 10.1002/ange.201504956

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A Metal-Free Synthesis of N-Aryl Carbamates under Ambient Conditions

Journal article published in 2015 by Wusheng Guo, Joan Gónzalez-Fabra, Nuno A. G. Bandeira ORCID, Carles Bo ORCID, Arjan W. Kleij
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This paper is available in a repository.

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Abstract

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.