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

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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.

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

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Article information


Submitted
20 Dec 2019
Accepted
28 Feb 2020
First published
28 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

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

T. Sugiishi, C. Matsumura and H. Amii, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02713K

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