Rhodium(III)-Catalyzed Synthesis of Diverse Fluorescent Polycyclic Purinium Salts from 6-Arylpurine Nucleosides and Alkynes

Org Lett. 2022 Jun 17;24(23):4234-4239. doi: 10.1021/acs.orglett.2c01546. Epub 2022 Jun 6.

Abstract

Described herein is an efficient strategy for assembling a new library of functionalized polycyclic purinium salts with a wide range of anions through RhIII-catalyzed C-H activation/annulation of 6-arylpurine nucleosides with alkynes under mild reaction conditions. The resulting products displayed tunable photoluminescence covering most of the visible spectrum. Mechanistic insights delineated the rhodium catalyst's mode of action. A purinoisoquinolinium-coordinated rhodium(I) sandwich complex was well characterized and identified as the key intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes
  • Catalysis
  • Nucleosides
  • Rhodium*
  • Salts

Substances

  • Alkynes
  • Nucleosides
  • Salts
  • Rhodium