Acid-catalyzed conjugate additions to 3-fluorobutenone

Meerwein arylation with 3-fluorobutenone

“…We have only found records of iodo-fluoro methanes and ethanes and some minor products from iodofluorination [9]. In comparison of the F NMR chemical shifts of products 9a-9f with a similar noniodinated compound [6], we find that the fluoro-iodo compounds are approximately 67 ppm downfield from hydro-fluoro compound. The large deshielding effect of iodine atoms on proton NMR spectroscopy is reported in the literature and apparently holds also for fluorine NMR [10].…”

“…Our recent studies on the chemistry of 3-fluorobutenone (7) [4][5][6] led us to investigate the Meerwein arylation of this fluorinated unsaturated system (Scheme 3). Although several non-activated vinyl fluorides have been studied in the Meerwein reaction [7], 7 is the first activated fluoroalkene.…”

Cycloaddition reactions of 3-fluorobutenone

“…We recently reported the preparation and synthetic utility of 3-fluorobutenone (8) in the Heck reaction [6] and in conjugate addition reactions [7]. Dienophile 8 is a fluorinated analog of methyl vinyl ketone.…”

Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid

“…[1][2][3][4][5][6][7][8][9] There are a few examples about the selectivity tuning for the reaction of hydroxybenzenes with α,β-unsaturated compounds, however, these precedents did not give satisfactory results. Rudolf Aumann discovered that both oxa-Michael adduct and Friedel-Crafts alkylated product were produced from the reaction of 9-phenanthrol, while the reaction of phenol only afforded the oxa-Michael adduct.…”