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

Bhilare, S., Gayakhe, V., Ardhapure, A., Sanghvi, Y., Schulke, C., Borozdina, Y., et al. (2016). Novel water-soluble phosphatriazenes: versatile ligands for Suzuki–Miyaura, Sonogashira and Heck reactions of nucleosides. RSC Advances, 6(87), 83820-83830. doi:10.1039/C6RA19039A.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0000-7A4A-5 Version Permalink: http://hdl.handle.net/21.11116/0000-0000-7A4B-4
Genre: Journal Article

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Bhilare, S, Author
Gayakhe, V, Author
Ardhapure, AV, Author
Sanghvi, YS, Author
Schulke, C, Author
Borozdina, Y1, Author              
Kapdi, AR, Author
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1Max Planck Institute for Biological Cybernetics, Max Planck Society, ou_1497794              

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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.

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 Dates: 2016-01
 Publication Status: Published in print
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 Identifiers: DOI: 10.1039/C6RA19039A
BibTex Citekey: BhilareGASSBK2016
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Title: RSC Advances
Source Genre: Journal
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Pages: - Volume / Issue: 6 (87) Sequence Number: - Start / End Page: 83820 - 83830 Identifier: -