N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes.

The N-heterocyclic carbene-catalyzed radical relay enables the vicinal alkylacylation of styrenes, acrylates and acrylo-nitrile using aldehydes and tertiary alkyl carboxylic acid-derived redox-active esters. This protocol introduces tertiary alkyl groups and acyl groups to C-C double bonds with complete regioselectivity to produce functionalized ketone derivatives. The radical relay mechanism involves single electron transfer from the enolate form of a Breslow interme-diate and radical addition of the resultant alkyl radical to the alkene followed by radical-radical coupling.

• Publication year

  2019

• Venue

  Journal of the American Chemical Society

• Publication date

  2019-08-26

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/jacs.9b07194PMID 31449757
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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