Fluorocyclization of unsaturated compounds tethered to heteroatom nucleophiles provides one of the most powerful and attractive methods for the synthesis of fluorine-containing heterocyclic compounds. For these reactions, metal-catalysts such as Pd and Au have been often employed, although the iodine(III)-catalyzed reactions of alkenyl amines have been reported as metal-free methods. On the other hand, we have recently developed a fluorocyclization of N-propargyl carboxamides as a first example for metal-free and catalytic fluorinative transformations of alkynes. However, there is a room for the improvement of product yields and substrate scope of our previous method. Considering the enhancement of stability and turnover of iodine(III) catalysts, we examined iodine(III) catalysts bearing coordinating substituents. Herein, we present the fluorocyclization of N-propargyl carboxamides using iodine(III) species in situ generated from iodoarene having coordinating substituents at ortho-positions in the presence of Selectfluor and HF-pyridine.

Fluorocyclization of N-propargyl carboxamides by iodine(III) catalysts bearing coordinating substituents

2019 Fall National Meeting

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