By the same authors

Interrogation of a Sonogashira Cross-Coupling of 8-Bromoguanosine with Phenylacetylene on Amberlite: Evidence for Pd/Cu Ion Binding and Propagation of Pd/Cu Nanoparticles

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JournalNucleosides, Nucleotides and Nucleic Acids
DatePublished - Feb 2011
Issue number2
Volume30
Number of pages17
Pages (from-to)168-184
Original languageEnglish

Abstract

The reactivity of Amberlite (IRA-67) base oheterogeneouso resin in Sonogashira cross-coupling of 8-bromoguanosine 1 with phenylacetylene 3 to give 2 has been examined. Both 1 and 2 coordinate to Pd and Cu ions, which explains why at equivalent catalyst loadings, the homogeneous reaction employing triethylamine base is poor yielding. X-ray photo-electron spectroscopy (XPS) has been used to probe and quantify the active nitrogen base sites of the Amberlite resin, and postreaction Pd and Cu species. The PdCl2(PPh3)2 precatalyst and CuI cocatalyst degrade to give Amberlite-supported metal nanoparticles (average size 2.7 nm). The guanosine product 2 formed using the Amberlite Pd/Cu catalyst system is of higher purity than reactions using a homogeneous Pd precatalyst, a prerequisite for use in biological applications.

    Research areas

  • Nucleoside, alkyne, palladium, cross-coupling, inhibition, catalyst recycling, PALLADIUM NANOPARTICLES, CHEMISTRY, NUCLEOSIDES, REACTIVITY, COMPLEXES, GUANOSINE, ACETYLENES, MOLECULES, CATALYSIS, THYMIDINE

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