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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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Publication details

The article was received on 07 May 2014, accepted on 23 May 2014 and first published on 23 May 2014


Article type: Communication
DOI: 10.1039/C4OB00945B
Citation: Org. Biomol. Chem., 2014,12, 5082-5088
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    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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