The synthesis of fluorinated building blocks is important in synthetic organic and pharmaceutical chemistry. Although these compounds are widely used, the efficient synthesis of trifluoromethylated compounds can still be challenging. In our work, we designed a novel alkenyliodonium salt as a trifluoroalkenyl synthon. Without the need of transition metal catalysis, we synthesized various N-substituted 2-trifluoromethyl aziridines in one-step reaction, under mild conditions directly from aryl and alkyl amines. In our further research we successfully widened the utility of our hypervalent reagent in organic synthesis as an electrophilic reagent in its reactions with various heteroatom nucleophiles. We found the optimal conditions to be slightly different, we explored the scope of the reaction to find it a robust, easily reproducible method without almost no steric and electronic limitation regarding the primer and seconder amine, heteroaromatic substrates. Additionally, the reaction mechanisms were examined by quantum chemical calculations.

Hypervalency aided route to 3,3,3-trifluoropropenylated heterocycles, 1,2-diamines and N-aryl-2-(trifluoromethyl)aziridines

2019 Spring National Meeting

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