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

Firth, Andrew G., Wilson, Karen, Baumann, Christoph G. and Fairlamb, Ian J. S. 2011. 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. Nucleosides, Nucleotides & Nucleic Acids 30 (2) , pp. 168-184. 10.1080/15257770.2010.548844

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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 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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Cardiff Catalysis Institute (CCI) Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Nucleoside, alkyne, palladium, cross-coupling, inhibition, catalyst recycling
Publisher:	Taylor & Francis
ISSN:	1525-7770
Last Modified:	19 Mar 2016 22:28
URI:	https://orca.cardiff.ac.uk/id/eprint/17373

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