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

Alistair J. MacNair, [No Value] Ming-Ming Tran, Jennifer E. Nelson, G. Usherwood Sloan, Alan Ironmonger, Stephen P. Thomas*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)5082-5088
JournalOrganic & Biomolecular chemistry
Volume12
Issue number28
Early online date23 May 2014
DOIs
Publication statusPublished - 28 Jul 2014

Keywords

  • LITHIUM ALUMINUM-HYDRIDE
  • AROMATIC NITRO-COMPOUNDS
  • SODIUM-BOROHYDRIDE
  • CHEMOSELECTIVE REDUCTION
  • SELECTIVE REDUCTION
  • UNACTIVATED ALKENES
  • RADICAL-ANION
  • NITROARENES
  • NITROBENZENE
  • ALKYNES

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