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

Literature Information

Publication Date 2018-08-29
DOI 10.1039/C8OB01653D
Impact Factor 3.876
Authors

Beatriz Lantaño, Sebastián Barata-Vallejo, Al Postigo


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Abstract

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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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