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

Molecules

Yong Liang²  Stanislaw F. Wnuk¹ 

[1] Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA; E-Mail

关键词: C-H activation;    cross-coupling;    direct arylation;    nucleosides;    purines;    pyrimidines;   

DOI  :  10.3390/molecules20034874

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.