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

Bhilare, S; Gayakhe, V; Ardhapure, AV; Sanghvi, YS; Schulke, C; Borozdina, YB; Kapdi, AR

doi:10.1039/C6RA19039A

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

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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.

Cite as: https://hdl.handle.net/21.11116/0000-0000-7A4A-5

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.