Superelectrophilic activation in superacid HF/SbF^sub 5^: Expanding molecular diversity in nitrogen-containing compounds series by fluorination

In superacid, such as HF/SbF5, functionalized organic molecules can be (poly)protonated to deliver cationic species which can react with very poor nucleophiles. This superelectrophilic activation can be applied to the development of unprecedented organic reactions. Through the use of ammonium-carben...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2018-10, Vol.214, p.68
Main Authors: Michelet, Bastien, Carreyre, Hélène, Lecornué, Frédéric, Mingot, Agnès, Thibaudeau, Sébastien
Format: Article
Language:English
Subjects:
Acids
Activation
Ammonium
Bioactive compounds
Biotechnology
Chemical reactions
Fluorination
Genomes
Nitrogen
Nucleophiles
Organic chemistry
Pharmaceuticals
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Summary:In superacid, such as HF/SbF5, functionalized organic molecules can be (poly)protonated to deliver cationic species which can react with very poor nucleophiles. This superelectrophilic activation can be applied to the development of unprecedented organic reactions. Through the use of ammonium-carbenium dications, activated keteniminium, or other modes of superelectrophilic activation, fluorinated nitrogen-containing building blocks can be efficiently generated. This mode of activation can also be applied for the late-stage insertion of fluorinated moieties on elaborated synthetic or natural bioactive compounds.
ISSN:0022-1139
1873-3328