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.
Highlights
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
Considering the importance of this moiety, the development of methods for the construction of vicinal diamines is an important area of research in organic synthesis[1,2]
Among the various synthetic possibilities of accessing the target diamine molecules, conceptually, the most straightforward way is the direct introduction of nitrogen atoms across a carbon–carbon double bond (Fig. 1c)[1,5]
Summary
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. Regarding the abundant N-atom sources, nucleophilic difunctionalization of alkenes with simple amines without the use of transition metals would be a cornerstone to improve structural diversity of diamine synthesis. This vicinal amination of the carbon–carbon double bond under metal free conditions has been presented with bifunctional nucleophiles in an intramolecular manner to afford N,N- and N,O-heterocyclic systems using alkenyl-sulfonium salts with two adjacent electrophilic centers[29,30,31,32]. The major challenge of the present approach is the selective heterodiamination with two different nitrogen nucleophiles due to the control of reactivity of the nucleophiles and intermediates
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