Benzylic Fluorination of Aza-Heterocycles Induced by Single-Electron Transfer to Selectfluor.

A selective and mild method for the benzylic fluorination of aromatic azaheterocycles with Selectfluor is described. These reactions take place by a previously unreported mechanism, in which electron transfer from the heterocyclic substrate to the electrophilic fluorinating agent Selectfluor eventually yields a benzylic radical, thus leading to the desired C-F bond formation. This mechanism enables high intra- and intermolecular selectivity for aza-heterocycles over other benzylic components with similar C-H bond-dissociation energies.

• Publication year

  2018

• Venue

  Angewandte Chemie

• Publication date

  2018-04-23

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.201801280PMID 29486098
• 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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