Iron-Catalysed Chemo-, Regio-, and Stereoselective Hydrosilylation of Alkenes and Alkynes using a Bench-Stable Iron(II) Pre-Catalyst

Mark D. Greenhalgh, Dominik J. Frank, Stephen P. Thomas

Research output: Contribution to journalArticlepeer-review

Abstract

The chemo-, regio-, and stereoselective iron-catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41-96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ, thus providing a simple and practical methodology for iron-catalysed hydrosilylation. The silane products can be oxidised to the anti-Markovnikov product of olefin hydration, and the one-pot iron-catalysed hydrosilylation-oxidation of olefins to give silane(di)ols directly is also reported. The iron pre-catalyst was used at loadings as low as 0.07mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000molh-1. Initial mechanistic studies indicate an iron(I) active catalyst.

Original languageEnglish
Pages (from-to)584-590
JournalAdvanced Synthesis & Catalysis
Volume356
Issue number2-3
Early online date2 Feb 2014
DOIs
Publication statusPublished - 10 Feb 2014

Keywords

  • catalysis
  • hydrosilylation
  • iron
  • olefins
  • synthetic methods
  • CROSS-COUPLING REACTIONS
  • ORGANIC-SYNTHESIS
  • EFFICIENT HYDROSILYLATION
  • SILAFUNCTIONAL COMPOUNDS
  • DEACTIVATION PATHWAYS
  • CARBONYL-COMPOUNDS
  • GRIGNARD-REAGENTS
  • HYDROXY GROUP
  • COMPLEXES
  • REDUCTION

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