Issue 7, 2011

Palladium nanoparticle-modified carbon nanotubes for electrochemical hydrogenolysis in ionic liquids

Abstract

The electrochemical hydrogenolysis of benzyl and carboxybenzyl protecting groups is described. Optimisation of a synthetic protocol afforded well-defined palladium (Pd) nanoparticles on the surface of multiwall carbon nanotubes (CNTs). The high surface area composite was investigated, and differences observed in the voltammetry for the same composite in aqueous and ionic liquid systems are discussed. When used to reduce acidic protons in the ionic liquid (IL) 1-ethy-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([C2mim][NTf2]) reactive palladium hydride was formed efficiently, which rapidly performed hydrogenolysis. The compounds 1-(3-(benzyloxy)propyl)-4-methoxybenzene, benzyl octyl carbonate, N,N′-bis(benzyloxycarbonyl)-L-lysine and N-benzyl-L-prolinol were investigated. Extended electrolysis of bis(trifluoromethylsulfonyl)imide (H[NTf2]) in [C2mim][NTf2] containing alcohol groups protected with benzyl and carboxybenzyl groups afforded the alcohol product in high yield. The probable hydrogenolysis of the similarly protected amine groups is also reported.

Graphical abstract: Palladium nanoparticle-modified carbon nanotubes for electrochemical hydrogenolysis in ionic liquids

Article information

Article type
Paper
Submitted
26 Jan 2011
Accepted
17 Mar 2011
First published
06 Apr 2011

New J. Chem., 2011,35, 1369-1375

Palladium nanoparticle-modified carbon nanotubes for electrochemical hydrogenolysis in ionic liquids

Y. Meng, L. Aldous, B. S. Pilgrim, T. J. Donohoe and R. G. Compton, New J. Chem., 2011, 35, 1369 DOI: 10.1039/C1NJ20070D

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