Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 40, Pages 11686-11690Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504956
Keywords
anilines; cyclic carbonates; hydrogen bonds; N-aryl carbamates; organocatalysis
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Funding
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ-2014-60419-R, CTQ2014-52824-R]
- Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- AGAUR [2014-SGR-409]
- COFUND [291787-ICIQ-IPMP]
- Cellex foundation
- ICREA Funding Source: Custom
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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 protonrelay mechanism mediated by the bicyclic guanidine base.
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