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Nucleosides, Nucleotides & Nucleic Acids Volume 26, 2007 - Issue 10-12
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Original Articles

Supported Synthesis and Functionnalization of 2″-Deoxyuridine by Suzuki-Miyaura Cross-Coupling

Saïd El Kazzouli Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d'Orléans, Orléans, France
,
Sabine Berteina-Raboin Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d'Orléans, Orléans, France
&
Luigi A. Agrofoglio Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d'Orléans, Orléans, France
Pages 1395-1398 | Published online: 05 Dec 2007
 
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Abstract

The synthesis and modification of 2′-deoxyuridine has been realized under Suzuki-Miyaura palladium-catalyzed cross-coupling conditions. Using Pd(PPh 3 ) 4 and Na 2 CO 3 , 5-iodo-2′-deoxyuridine bound to solid support is coupled with various boronic acids to give 5-(hetero)aryl-2′-deoxyuridine. Pd(PPh 3 ) 4 palladium catalyzed was found to be superior to Pd(OAc) 2 and (NHC)Pd(allyl)Cl for Suzuki-Miyaura palladium-catalyzed reactions.

Notes

a Conversions were calculated from 1H MNR of crude product after cleavage.

b Yields (after 5 steps).

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