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Molecules 2012, 17(12), 14409-14417; doi:10.3390/molecules171214409

Efficient Synthesis of Unprotected C-5-Aryl/Heteroaryl-2'-deoxyuridine via a Suzuki-Miyaura Reaction in Aqueous Media

Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 7311, BP 6759, 45067 Orléans Cedex 2, France
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Received: 8 October 2012 / Revised: 20 November 2012 / Accepted: 23 November 2012 / Published: 5 December 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl derivatives at the C5 position of unprotected 2'-deoxyuridine in the same media with a common catalyst system avoiding exotic ligands, since palladium acetate and triphenylphosphine afforded the expected products in moderate to good yields.
Keywords: unnatural nucleosides; Suzuki-Miyaura coupling; aqueous conditions unnatural nucleosides; Suzuki-Miyaura coupling; aqueous conditions
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Fresneau, N.; Hiebel, M.-A.; Agrofoglio, L.A.; Berteina-Raboin, S. Efficient Synthesis of Unprotected C-5-Aryl/Heteroaryl-2'-deoxyuridine via a Suzuki-Miyaura Reaction in Aqueous Media. Molecules 2012, 17, 14409-14417.

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