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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Yong Liang, Stanislaw F Wnuk

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.

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Citations

Aug 30, 2016·The Journal of Organic Chemistry·Qing HeStanislaw F Wnuk
Mar 2, 2017·The Journal of Organic Chemistry·Andreas GramlBurkhard König
Apr 3, 2019·Nucleosides, Nucleotides & Nucleic Acids·Annamalai SenthilvelanAnilkumar R Kore
Feb 23, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiangyou DongQiang Xiao
Apr 27, 2018·ACS Omega·Nazarii SabatMichal Hocek
Feb 28, 2018·The Journal of Organic Chemistry·Zhoulong FanAo Zhang
Sep 20, 2018·The Journal of Organic Chemistry·Danielle E FagnaniRonald K Castellano

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