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

Andrew G. Firth, Karen Wilson, Christoph G. Baumann, Ian J.S. Fairlamb

Research output: Contribution to journalArticle

Abstract

The reactivity of Amberlite (IRA-67) base "heterogeneous" 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 Pd2Cl3(PPh)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.
Original languageEnglish
Pages (from-to)168-184
Number of pages17
JournalNucleosides, Nucleotides and Nucleic Acids
Volume30
Issue number2
Early online date24 Dec 2010
DOIs
Publication statusPublished - 2011

Keywords

  • nucleoside
  • alkyne
  • palladium
  • cross-coupling
  • inhibition
  • catalyst recycling

Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.

  • Cite this