Synthesis of carbamates from carbon dioxide promoted by organostannanes and alkoxysilanes

A cooperative methoxy transfer between orthosilicate esters and organotin oxides was developed for the synthesis of various N-alkyl and N-aryl carbamates from carbon dioxide in up to 97% isolated yield. The reaction is highly selective and N-alkylated amines are not observed. Density functional theo...

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Hauptverfasser: Germain, Nicolas (VerfasserIn) , Trapp, Oliver (VerfasserIn) , Hermsen, Marko (VerfasserIn) , Schaub, Thomas (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 31 January 2017
In: Applied organometallic chemistry
Year: 2017, Jahrgang: 31, Heft: 10
ISSN:1099-0739
DOI:10.1002/aoc.3733
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/aoc.3733
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/aoc.3733
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Verfasserangaben:Nicolas Germain, Marko Hermsen, Thomas Schaub, Oliver Trapp
Beschreibung
Zusammenfassung:A cooperative methoxy transfer between orthosilicate esters and organotin oxides was developed for the synthesis of various N-alkyl and N-aryl carbamates from carbon dioxide in up to 97% isolated yield. The reaction is highly selective and N-alkylated amines are not observed. Density functional theory calculations of the reaction were performed and, together with NMR observations, a plausible mechanism featuring the catalytic regeneration of dialkyltin dialkoxide is proposed.
Beschreibung:Gesehen am 14.05.2018
Beschreibung:Online Resource
ISSN:1099-0739
DOI:10.1002/aoc.3733