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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.

SUBMITTER: MacNair AJ

PROVIDER: S-EPMC4295815 | biostudies-other | 2014 Jul

REPOSITORIES: biostudies-other

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

MacNair Alistair J AJ Tran Ming-Ming MM Nelson Jennifer E JE Sloan G Usherwood GU Ironmonger Alan A Thomas Stephen P SP

Organic & biomolecular chemistry 20140701 28

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. ...[more]

PMID: 24914735

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