Synthesis of 3-fluoro-2,5-disubstituted furans through ring expansion of gem-difluorocyclopropyl ketones

Literature Information

Publication Date 2020-02-28
DOI 10.1039/C9OB02713K
Impact Factor 3.876
Authors

Tsuyuka Sugiishi, Chihori Matsumura, Hideki Amii


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Abstract

The synthesis of 3-fluoro-2,5-disubstituted furans from gem-difluorocyclopropyl ketones was accomplished using trifluoromethanesulfonic acid (CF3SO3H) through ring expansion owing to the activation of the carbonyl group in the starting material. The present synthesis of 3-fluorofurans tolerates substrates designed for products with aromatic substituents at the C-2 and C-5 positions.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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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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