First catalyst-free CO2 trapping of N-acyliminium ions under ambient conditions: sustainable multicomponent synthesis of thia- and oxazolidinyl carbamates

The first trapping of N-acyliminium ions by in situ generated carbaminic acid (product of carbon dioxide (CO2) and amine) is reported. This catalyst-free reaction provides a convenient and feasible approach to prepare N-acyl thia- and oxazolidinyl carbamates with good functional-group compatibility...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 16; no. 37; pp. 8292 - 8304
Main Authors Franz, Max, Stalling, Timo, Steinert, Henning, Martens, Jürgen
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 2018
Subjects
Carbamates (tradename)
Carbon dioxide
Catalysis
Catalysts
Chemical synthesis
NMR
Nuclear magnetic resonance
Substrates
Trapping
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Summary:The first trapping of N-acyliminium ions by in situ generated carbaminic acid (product of carbon dioxide (CO2) and amine) is reported. This catalyst-free reaction provides a convenient and feasible approach to prepare N-acyl thia- and oxazolidinyl carbamates with good functional-group compatibility and high efficiency under green conditions. Furthermore, the multicomponent method features a broad substrate scope, facile product diversification, smooth scale-up and notable potential for polymer applications.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01865k