Vicinal difunctionalization of carbon–carbon double bond for the platform synthesis of trifluoroalkyl amines

Ferenc Béke, Ádám Mészáros, Ágnes Tóth, Bence Béla Botlik and Zoltán Novák ()
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Ferenc Béke: Eötvös Loránd University
Ádám Mészáros: Eötvös Loránd University
Ágnes Tóth: Eötvös Loránd University
Bence Béla Botlik: Eötvös Loránd University
Zoltán Novák: Eötvös Loránd University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract Regioselective vicinal diamination of carbon–carbon double bonds with two different amines is a synthetic challenge under transition metal-free conditions, especially for the synthesis of trifluoromethylated amines. However, the synthesis of ethylene diamines and fluorinated amine compounds is demanded, especially in the pharmaceutical sector. Herein, we demonstrate that the controllable double nucleophilic functionalization of an activated alkene synthon, originated from a trifluoropropenyliodonium salt with two distinct nucleophiles, enables the selective synthesis of trifluoromethylated ethylene amines and diamines on broad scale with high efficiency under mild reaction conditions. Considering the chemical nature of the reactants, our synthetic approach brings forth an efficient methodology and provides versatile access to highly fluorinated amines.

Date: 2020
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DOI: 10.1038/s41467-020-19748-z

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