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Molecules 2015, 20(3), 4874-4901; doi:10.3390/molecules20034874

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
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)

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. 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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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