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A Metal‐Free Synthesis of N‐Aryl Carbamates under Ambient Conditions
Author(s) -
Guo Wusheng,
GónzalezFabra Joan,
Bandeira Nuno A. G.,
Bo Carles,
Kleij Arjan W.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201504956
Subject(s) - synthon , chemistry , aryl , guanidine , carbamate , reactivity (psychology) , combinatorial chemistry , bicyclic molecule , organic chemistry , organic synthesis , catalysis , alternative medicine , medicine , alkyl , pathology
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.