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Issue 31, 2015
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Pd–imidate complexes as recyclable catalysts for the synthesis of C5-alkenylated pyrimidine nucleosides via Heck cross-coupling reaction

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Abstract

Pd–imidate complexes have been employed as efficient catalysts for the Heck alkenylation of unprotected 5-iodo-2′-deoxyuridine in acetonitrile. The protocol was also shown to work well for the unprotected 5-iodo-2′-deoxycytidine. A highly efficient scale-up synthesis of the HSV-1 inhibitor Brivudine (BVDU) is also accomplished in an overall yield of 72% over 3-steps. The catalyst also showed recyclability for 3 consecutive runs.

Graphical abstract: Pd–imidate complexes as recyclable catalysts for the synthesis of C5-alkenylated pyrimidine nucleosides via Heck cross-coupling reaction

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Supplementary files

Article information


Submitted
25 Jan 2015
Accepted
27 Feb 2015
First published
27 Feb 2015

RSC Adv., 2015,5, 24558-24563
Article type
Paper

Pd–imidate complexes as recyclable catalysts for the synthesis of C5-alkenylated pyrimidine nucleosides via Heck cross-coupling reaction

A. V. Ardhapure, Y. S. Sanghvi, A. R. Kapdi, J. García, G. Sanchez, P. Lozano and J. L. Serrano, RSC Adv., 2015, 5, 24558
DOI: 10.1039/C5RA01461A

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