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α‐Fluorotricarbonyl Derivatives as Versatile Fluorinated Building Blocks: Synthesis of Fluoroacetophenone, Fluoroketo Ester and Fluoropyran‐4‐one Derivatives
Author(s) -
Harsanyi Antal,
Lückener Anne,
Pasztor Hedvig,
Yilmaz Zahide,
Tam Lawrence,
Yufit Dmitry S.,
Sandford Graham
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000503
Subject(s) - chemistry , selectfluor , acetophenone , meldrum's acid , phenacyl , electrophile , pyran , organic chemistry , reagent , phenacyl bromide , electrophilic fluorination , ethanol , diketone , combinatorial chemistry , catalysis
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.