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γ-C (sp)-H bond functionalisation of α,β-unsaturated amides through an umpolung strategy. | LitMetric

AI Article Synopsis

  • A new method has been created for the nucleophilic γ-phenylation and γ-alkylation of α,β-unsaturated amides.
  • This reaction involves introducing phenyl and alkyl groups to a vinylketene N,O-acetal, which is produced directly from an α,β-unsaturated N-alkoxyamide.
  • The process consists of two steps but is conducted in a single pot by cleaving the N-O bond.

Article Abstract

The nucleophilic γ-phenylation and γ-alkylation of α,β-unsaturated amides have been developed. This umpolung reaction allows the regioselective introduction of phenyl and alkyl groups to a vinylketene N,O-acetal, which is generated in situ from an α,β-unsaturated N-alkoxyamide, followed by N-O bond cleavage in a two-step, one-pot process.

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Source
http://dx.doi.org/10.1039/d0ob00125bDOI Listing

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