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Issue 87, 2016, Issue in Progress
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Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides

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Abstract

Two new water-soluble phosphatriazene ligands have been synthesized as versatile ligands for complexation reactions with Pd(OAc)2 and utilized for catalyzing column-free Suzuki–Miyaura cross-coupling of various purine and pyrimidine halonucleosides in water. The water-solubility of the catalytic system simplified the isolation of the cross-coupled products to mere filtration, while the catalytically active solution in the filtrate was recycled eight times. A novel copper-free Sonogashira coupling protocol for the nucleosides has also been established via a one-pot synthesis of FV-100, a nucleoside-based drug in phase 3 clinical trials for herpes zoster or shingles treatment. Application of the Heck reaction was demonstrated by the synthesis of another antiviral drug: BVDU.

Graphical abstract: Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides

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Supplementary files

Article information


Submitted
27 Jul 2016
Accepted
26 Aug 2016
First published
29 Aug 2016

RSC Adv., 2016,6, 83820-83830
Article type
Paper

Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides

S. Bhilare, V. Gayakhe, A. V. Ardhapure, Y. S. Sanghvi, C. Schulzke, Y. Borozdina and A. R. Kapdi, RSC Adv., 2016, 6, 83820
DOI: 10.1039/C6RA19039A

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