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

Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA
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Author to whom correspondence should be addressed.
Academic Editor: Mahesh Lakshman
Molecules 2015, 20(3), 4874-4901; https://doi.org/10.3390/molecules20034874
Received: 15 February 2015 / Revised: 11 March 2015 / Accepted: 13 March 2015 / Published: 17 March 2015
(This article belongs to the Special Issue Nucleoside Modifications)
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. View Full-Text
Keywords: C-H activation; cross-coupling; direct arylation; nucleosides; purines; pyrimidines C-H activation; cross-coupling; direct arylation; nucleosides; purines; pyrimidines
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MDPI and ACS Style

Liang, Y.; Wnuk, S.F. Modification of Purine and Pyrimidine Nucleosides by Direct C-H Bond Activation. Molecules 2015, 20, 4874-4901.

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