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

Organic & Biomolecular Chemistry
Tsuyuka SugiishiHideki Amii

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.

References

May 18, 2001·Journal of Medicinal Chemistry·C E StephensD W Boykin
Apr 9, 2008·The Journal of Organic Chemistry·Wei XuJose Salazar
Oct 2, 2008·The Journal of Organic Chemistry·Xiao-Chun HangJi-Chang Xiao
Apr 2, 2011·The Journal of Organic Chemistry·William R DolbierWei Xu
Jan 21, 2012·Organic & Biomolecular Chemistry·Yan LiRoman Dembinski
Jan 12, 2013·Chemical Reviews·Anton V GulevichVladimir Gevorgyan
Sep 14, 2013·Chemical Communications : Chem Comm·Tang-Po YangJi-Chang Xiao
Jan 21, 2014·Journal of the American Chemical Society·Xu-Hui JinMichael Bendikov
Jan 29, 2014·Angewandte Chemie·Ori Gidron, Michael Bendikov

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Citations

Feb 11, 2021·Beilstein Journal of Organic Chemistry·Kymbat S AdekenovaSergazy M Adekenov
Jun 3, 2021·Organic & Biomolecular Chemistry·Angelina Yu BobrovaYury V Tomilov

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Methods Mentioned

BETA
NMR

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