a-Fluorotricarbonyl derivatives as versatile fluorinated building blocks: synthesis of fluoro-acetophenone, fluoro-ketoester and fluoro-pyran-4-one derivatives

Harsanyi, Antal; Lueckener, Anne; Pasztor, Hedvig; Yilmaz, Zahide; Tam, Lawrence; Yufit, Dmitry; S*andford, Graham

doi:10.1002/ejoc.202000503

a-Fluorotricarbonyl derivatives as versatile fluorinated building blocks: synthesis of fluoro-acetophenone, fluoro-ketoester and fluoro-pyran-4-one derivatives

Harsanyi, Antal; Lueckener, Anne; Pasztor, Hedvig; Yilmaz, Zahide; Tam, Lawrence; Yufit, Dmitry; S*andford, Graham

Authors

Antal Harsanyi

Anne Lueckener

Hedvig Pasztor

Zahide Yilmaz

Lawrence Tam

Dr Dmitry Yufit d.s.yufit@durham.ac.uk
Academic Visitor

Graham S*andford

Contributors

G Sandford graham.sandford@durham.ac.uk
Other

Abstract

Fluorinated acyl‐Meldrum’s acid derivatives were synthesised by electrophilic fluorination of appropriate phenacyl Meldrum’s acid substrates using Selectfluor. Reactions with water, ethanol, Grignard and alkynyl lithium reagents gave rise to the corresponding fluoro‐acetophenone, ‐1,3‐ketoester, ‐1,3‐diketone and ‐pyran‐4‐one products respectively from the same selectively fluorinated scaffold in one‐step procedures.

Citation

Harsanyi, A., Lueckener, A., Pasztor, H., Yilmaz, Z., Tam, L., Yufit, D., & S*andford, G. (2020). a-Fluorotricarbonyl derivatives as versatile fluorinated building blocks: synthesis of fluoro-acetophenone, fluoro-ketoester and fluoro-pyran-4-one derivatives. European Journal of Organic Chemistry, 2020(25), 3872-3878. https://doi.org/10.1002/ejoc.202000503

Journal Article Type	Article
Acceptance Date	May 13, 2020
Online Publication Date	Jun 4, 2020
Publication Date	Jul 7, 2020
Deposit Date	May 19, 2020
Publicly Available Date	Jul 1, 2020
Journal	European Journal of Organic Chemistry
Print ISSN	1434-193X
Electronic ISSN	1099-0690
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	2020
Issue	25
Pages	3872-3878
DOI	https://doi.org/10.1002/ejoc.202000503

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© 2020 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.