Pd-Xantphos-catalyzed direct arylation of nucleosides

Org Lett. 2006 Sep 28;8(20):4613-6. doi: 10.1021/ol0619516.

Abstract

Direct arylation of the exocyclic amino groups of nucleosides represents a simple approach to N-aryl nucleoside derivatives. To date, one limitation has been that only electron-deficient aryl bromides and triflates possessed adequate reactivity for efficient, direct N-arylation of nucleosides. We demonstrate herein that Pd-Xantphos catalytic systems lead to successful N-arylation of suitably protected 2'-deoxyadenosine and 2'-deoxyguanosine with a wide range of aryl bromides.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Magnetic Resonance Spectroscopy
  • Nucleosides / chemistry*
  • Palladium / chemistry*
  • Phosphines / chemistry*
  • Xanthenes / chemistry*

Substances

  • Nucleosides
  • Phosphines
  • Xanthenes
  • Palladium
  • xantphos