Molecules (Mar 2015)

Modification of Purine and Pyrimidine Nucleosides by Direct C-H Bond Activation

  • Yong Liang,
  • Stanislaw F. Wnuk

DOI
https://doi.org/10.3390/molecules20034874
Journal volume & issue
Vol. 20, no. 3
pp. 4874 – 4901

Abstract

Read online

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.

Keywords