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Issue 28, 2014
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Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4

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Abstract

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(III) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

Graphical abstract: Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4

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Supplementary files

Article information


Submitted
07 May 2014
Accepted
23 May 2014
First published
23 May 2014

This article is Open Access

Org. Biomol. Chem., 2014,12, 5082-5088
Article type
Communication
Author version available

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4

A. J. MacNair, M. Tran, J. E. Nelson, G. U. Sloan, A. Ironmonger and S. P. Thomas, Org. Biomol. Chem., 2014, 12, 5082
DOI: 10.1039/C4OB00945B

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