Issue 28, 2014

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

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

Supplementary files

Article information

Article type
Communication
Submitted
07 May 2014
Accepted
23 May 2014
First published
23 May 2014
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2014,12, 5082-5088

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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