title: Modification of purine and pyrimidine nucleosides by direct C-H bond activation.
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.
authors: Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA. ylian004@fiu.edu.
authors: Yong
authors: Y
authors: Liang
authors: Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA. wnuk@fiu.edu.
authors: Stanislaw F
authors: SF
authors: Wnuk
mesh_terms: D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D011684:Purine Nucleosides / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000737:chemistry*
chemical_list: D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; D002244:Carbon; D006859:Hydrogen