Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 12, Pages 3084-3088Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711737
Keywords
alkali metals; carbodiimides; guanidines; isoureas; organocatalysis
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Funding
- CINES [sis6494]
- CHARMMMAT Laboratory of Excellence
- European Research Council (ERC) [336467]
- CEA
- CNRS
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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.
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