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Metal‐Free and Alkali‐Metal‐Catalyzed Synthesis of Isoureas from Alcohols and Carbodiimides
Author(s) -
Imberdis Arnaud,
Lefèvre Guillaume,
Thuéry Pierre,
Cantat Thibault
Publication year - 2018
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.201711737
Subject(s) - alkali metal , catalysis , chemistry , chelation , potassium , metal , transition metal , coordination sphere , inorganic chemistry , organic chemistry , polymer chemistry
The first addition of alcohols to carbodiimides catalyzed by transition‐metal‐free compounds employs 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 when TBDK is used as the catalyst. Control of the coordination sphere of potassium with exogenous chelating ligands, in combination with mechanistic DFT calculations, demonstrated the role and positive influence of the alkali‐metal cation on the kinetics.