Modification of purine and pyrimidine nucleosides by direct C-H bond activation

Molecules. 2015 Mar 17;20(3):4874-901. doi: 10.3390/molecules20034874.

Abstract

Transition metal-catalyzed modifications of the activated heterocyclic bases of nucleosides as well as DNA or RNA fragments employing traditional cross-coupling methods have been well-established in nucleic acid chemistry. This review covers advances in the area of cross-coupling reactions in which nucleosides are functionalized via direct activation of the C8-H bond in purine and the C5-H or C6-H bond in uracil bases. The review focuses on Pd/Cu-catalyzed couplings between unactivated nucleoside bases with aryl halides. It also discusses cross-dehydrogenative arylations and alkenylations as well as other reactions used for modification of nucleoside bases that avoid the use of organometallic precursors and involve direct C-H bond activation in at least one substrate. The scope and efficiency of these coupling reactions along with some mechanistic considerations are discussed.

Publication types

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

MeSH terms

  • Carbon / chemistry
  • Catalysis
  • Hydrogen / chemistry
  • Purine Nucleosides / chemistry*
  • Pyrimidine Nucleosides / chemistry*

Substances

  • Purine Nucleosides
  • Pyrimidine Nucleosides
  • Carbon
  • Hydrogen