Substitution effect on the hydrofluorination reaction of unsaturated amines in superacid HF/SbF5

Fei Liu; Agnès Martin-Mingot; Marie-Paule Jouannetaud; Omar Karam; Sébastien Thibaudeau

doi:10.1039/B915077C

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Organic & Biomolecular Chemistry

Issue 22, 2009

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Substitution effect on the hydrofluorination reaction of unsaturated amines in superacid HF/SbF₅

Fei Liu , Agnès Martin-Mingot , Marie-Paule Jouannetaud , Omar Karam and Sébastien Thibaudeau

Org. Biomol. Chem., 2009, 7, 4789-4797

DOI: 10.1039/B915077C
Received 24 Jul 2009, Accepted 26 Aug 2009
First published on the web 22 Sep 2009

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This paper describes the scope and limitations of the hydrofluorination reaction in superacid HF/SbF₅. On the basis of experimental studies of polyfunctional substrates’ behaviour, the dramatic effect of substitution on the superelectrophilic character of ammonium–carbenium dications was emphasized. This reaction was applied to the synthesis of novel fluorinated key building blocks. Furthermore, the hydrofluorination reaction and the discovered homodimerization/fluorination reaction were applied to the synthesis of highly valued fluorinated diamines.

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Fei Liu
Agnès Martin-Mingot
Marie-Paule Jouannetaud
Omar Karam
Sébastien Thibaudeau

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Organic & Biomolecular Chemistry

Substitution effect on the hydrofluorination reaction of unsaturated amines in superacid HF/SbF₅

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