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Organic dye-photocatalyzed fluoroalkylation of heteroarene-N-oxide derivatives.

Org Biomol Chem; 16(36): 6718-6727, 2018 Sep 19.
Artículo en Inglés | MEDLINE | ID: mdl-30183800
The first direct CHet-H perfluoroalkylation reaction of heteroaromatic-N-oxides has been achieved through a visible light-photocatalyzed reaction in the presence of commercially available perfluoroalkyl iodides RF-I and base in DMF as solvent and Rose Bengal as organic photocatalyst. The reactions proceed in the absence of transition metals and can be scaled up. Through an acid-catalyzed transformation of the perfluoroalkylated-N-oxides thus obtained, the first direct syntheses of 2-(perfluoroalkyl)benzo[f][1,3]oxazepines are achieved. De-oxygenation of the resulting perfluoroalkylated heteroaromatic-N-oxides leads to high yielding and regioselective radical perfluoroalkylation protocols of heteroaromatic compounds. To the best of our knowledge, this is the first report on a direct method for perfluoroalkylation of pyridine-, quinoline-, and diazine-N-oxide derivatives.