Decatungstate-photocatalysed C(sp3)-H azidation

Chem Commun (Camb). 2022 Apr 14;58(31):4869-4872. doi: 10.1039/d2cc00425a.

Abstract

C-H Azidation is an increasingly important tool for bioconjugation, materials chemistry, and the synthesis of nitrogen-containing natural products. While several approaches have been developed, these often require exotic and energetic reagents, expensive photocatalysts, or both. Here we report a simple and general C-H azidation reaction using earth-abundant tetra-n-butylammonium decatungstate as a photocatalyst and commercial p-acetamidobenzenesulfonyl azide (p-ABSA) as the azide source. This system can azidate a variety of unactivated C(sp3)-H bonds in moderate to good yields and excellent turnover numbers. Preliminary mechanistic experiments implicate a radical mechanism proceeding VIA photo-hydrogen atom transfer (photo-HAT).

MeSH terms

  • Azides* / chemistry
  • Catalysis
  • Hydrogen* / chemistry
  • Nitrogen / chemistry

Substances

  • Azides
  • Hydrogen
  • Nitrogen