2023 article
Divergent Synthesis of & beta;-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals
Jang, Y., Deng, W., Sprague, I. S. S., & Lindsay, V. N. G. (2023, July 6). Divergent Synthesis of & beta;-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals. ORGANIC LETTERS.
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Source: Web Of Science
Added: July 24, 2023
An expedient approach for the synthesis of challenging β-fluoroamides from readily accessible cyclopropanone equivalents is reported. Following the addition of pyrazole used here as a transient leaving group, silver-catalyzed regiospecific ring-opening fluorination of the resulting hemiaminal leads to a β-fluorinated N-acylpyrazole intermediate reactive to substitution with amines, ultimately affording β-fluoroamides. The process could also be extended to the synthesis of β-fluoroesters and γ-fluoroalcohols via the addition of alcohols or hydrides as terminal nucleophiles, respectively.