Reactions of hydrogen fluoride with diazo ketones

Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H–F Insertion

“…The Davies group has recently described a silver-catalyzed fluorination of vinyl diazoacetates with Et 3 N·3HF, but this transformation yields γ-fluoro-α,β-unsaturated carbonyl compounds rather than fluorinating at the carbenoid position . Direct fluorination of α-diazocarbonyl substrates may be accomplished with highly reactive and acidic HF-containing reagents. − Only simple, unfunctionalized substrates are tolerated, however, and translation to PET applications is challenging …”