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Ytterbium(II) as a mediator in organic electrosynthesis - possibilities and limitations

Ytterbium(II) as a mediator in organic electrosynthesis - possibilities and limitations
Ytterbium(II) as a mediator in organic electrosynthesis - possibilities and limitations
The kinetics of the Yb(III)/Yb(II) couple in aprotic solvents are rapid at several electrode materials and the reducing power of the Yb(II) may be modified substantially by choice of solvent and electrolyte. Electrogenerated Yb(II), when present in stoichiometric amounts, allows the stereoselective reduction of 1,3-dibenzoylpropane to the cis isomer of a cyclic diol. Ytterbium(III) is not, however, a straightforward 'mediator' because, after the reduction of 1,3-dibenzoylpropane by the Yb(H), the Yb(III) is bound to the organic product. Both use of an aluminium anode or addition of trimethylsilylbromide lead to release of the Yb(III); then the ytterbium acts as a catalyst. Such procedures, however, lead to loss in the stereoselectivity of the reduction and the reactions are slow so that the regeneration of the Yb(III) does not enhance the current density. The current density is always low, limited by mass transport of the catalyst.
mediated electrolysis, ytterbium(iii)/(ii), 1, 3-dibenzoylpropanesamarium(ii) iodide, reducing power, alkyl-halides, smi2, ketones, reduction, cosolvent, thf
0013-4686
1065-1071
Andreu, R.
1cf68e36-5642-4972-af21-3f050f83f752
Pletcher, D.
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Andreu, R.
1cf68e36-5642-4972-af21-3f050f83f752
Pletcher, D.
f22ebe69-b859-4a89-80b0-9e190e6f8f30

Andreu, R. and Pletcher, D. (2003) Ytterbium(II) as a mediator in organic electrosynthesis - possibilities and limitations. Electrochimica Acta, 48 (8), 1065-1071. (doi:10.1016/S0013-4686(02)00844-7).

Record type: Article

Abstract

The kinetics of the Yb(III)/Yb(II) couple in aprotic solvents are rapid at several electrode materials and the reducing power of the Yb(II) may be modified substantially by choice of solvent and electrolyte. Electrogenerated Yb(II), when present in stoichiometric amounts, allows the stereoselective reduction of 1,3-dibenzoylpropane to the cis isomer of a cyclic diol. Ytterbium(III) is not, however, a straightforward 'mediator' because, after the reduction of 1,3-dibenzoylpropane by the Yb(H), the Yb(III) is bound to the organic product. Both use of an aluminium anode or addition of trimethylsilylbromide lead to release of the Yb(III); then the ytterbium acts as a catalyst. Such procedures, however, lead to loss in the stereoselectivity of the reduction and the reactions are slow so that the regeneration of the Yb(III) does not enhance the current density. The current density is always low, limited by mass transport of the catalyst.

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More information

Published date: 5 April 2003
Keywords: mediated electrolysis, ytterbium(iii)/(ii), 1, 3-dibenzoylpropanesamarium(ii) iodide, reducing power, alkyl-halides, smi2, ketones, reduction, cosolvent, thf

Identifiers

Local EPrints ID: 19881
URI: http://eprints.soton.ac.uk/id/eprint/19881
ISSN: 0013-4686
PURE UUID: ea89b41f-476f-400a-8f30-736af88d15ed

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Date deposited: 23 Feb 2006
Last modified: 09 Jan 2022 04:55

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Contributors

Author: R. Andreu
Author: D. Pletcher

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