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Substrate-controlled product divergence in the reaction of α-fluoro-β-ketoamides with arynes.

An interesting substrate-controlled reactivity switch has been observed in the reaction of α-fluoro-β-ketoamides with arynes. The reaction of secondary α-fluoro-β-ketoamides with arynes provided access to α-aryl-α-fluoroacetamides through an arylation/deacylation sequence.… Click to show full abstract

An interesting substrate-controlled reactivity switch has been observed in the reaction of α-fluoro-β-ketoamides with arynes. The reaction of secondary α-fluoro-β-ketoamides with arynes provided access to α-aryl-α-fluoroacetamides through an arylation/deacylation sequence. Interestingly, the reaction of tertiary α-fluoro-β-ketoamides resulted in the C-C σ-bond insertion reaction to afford 1,2-disubstituted arenes.

Keywords: reaction; reaction fluoro; ketoamides arynes; fluoro ketoamides; substrate controlled

Journal Title: Chemical communications
Year Published: 2022

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