Α‐Fluorotricarbonyl Derivatives as Versatile Fluorinated Building Blocks: Synthesis of Fluoroacetophenone, Fluoroketo Ester and Fluoropyran‐4‐one Derivatives. Issue 25 (4th June 2020)

• Record Type: Journal Article
• Authors: Harsanyi, Antal; Lückener, Anne; Pasztor, Hedvig; Yilmaz, Zahide; Tam, Lawrence; Yufit, Dmitry S.; Sandford, Graham
• Is Part Of: European journal of organic chemistry. Issue 25(2020)
• Page Start: 3872
• Page End: 3878
• Publication Date: 2020-06-04
• Subjects: Building blocks -- Fluorinated compounds -- Fluorine -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000503
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Fluorinated acyl‐Meldrum's acid derivatives were synthesized by electrophilic fluorination of appropriate phenacyl Meldrum's acid substrates using Selectfluor. Reactions with water, ethanol, Grignard, and alkynyllithium reagents gave rise to the corresponding fluoro‐acetophenone, –1, 3‐keto ester, –1, 3‐diketone and ‐pyran‐4‐one products respectively from the same selectively fluorinated scaffold in one‐step procedures. Abstract : Fluorinated acyl Meldrum's acid derivatives, synthesized by electrophilic fluorination react with nucleophiles to give fluoroacetophenones, 2‐fluoro‐1, 3‐keto ester, 2‐fluoro‐1, 3‐diketone and fluoropyran‐4‐one products from the same fluorinated scaffold.