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

Harsanyi, Antal; Luckener, Anne; Pasztor, Hedvig; Yilmaz, Zahide; Tam, Lawrence; Yufit, Dmitry; Sandford, Graham

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., Luckener, A., Pasztor, H., Yilmaz, Z., Tam, L., Yufit, D., & Sandford, 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
• Public URL: https://durham-repository.worktribe.com/output/1270474