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

TY - JOUR

T1 - Interrogation of a Sonogashira Cross-Coupling of 8-Bromoguanosine with Phenylacetylene on Amberlite

T2 - Evidence for Pd/Cu Ion Binding and Propagation of Pd/Cu Nanoparticles

AU - Firth, Andrew G.

AU - Wilson, Karen

AU - Baumann, Christoph G.

AU - Fairlamb, Ian J. S.

PY - 2011/2

Y1 - 2011/2

N2 - 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.

AB - 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.

KW - Nucleoside

KW - alkyne

KW - palladium

KW - cross-coupling

KW - inhibition

KW - catalyst recycling

KW - PALLADIUM NANOPARTICLES

KW - CHEMISTRY

KW - NUCLEOSIDES

KW - REACTIVITY

KW - COMPLEXES

KW - GUANOSINE

KW - ACETYLENES

KW - MOLECULES

KW - CATALYSIS

KW - THYMIDINE

UR - http://www.scopus.com/inward/record.url?scp=79952168698&partnerID=8YFLogxK

U2 - 10.1080/15257770.2010.548844

DO - 10.1080/15257770.2010.548844

M3 - Article

SN - 1525-7770

VL - 30

SP - 168

EP - 184

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 2

ER -