One-pot reduction of aryl iodides using 4-dmap methiodide salt

J. Garnier, J.A. Murphy, S.Z. Zhou, A.T. Turner, EPRSC (Funder), University of Strathclyde (Funder), AstraZeneca (Funder)

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

An efficient one-pot procedure is described for the reduction of aryl iodides to aryl anions using a structurally simple bis-pyridinylidene electron donor, prepared in situ by treating 4-DMAP methiodide salt with base. The results show (i) that pyridinylidene carbenes can be easily used for intermolecular C-C bond formation, (ii) that bis-pyridinylidenes demonstrate superior robustness compared to electron-donor systems based on bis-imidazolylidenes, and (iii) that electron-donor strength is enhanced in the simplified DMAP-based donor. Deuterated analogues of this donor also provide mechanistic information on the source of protons when the aryl anions are quenched in situ.
Original languageEnglish
Pages (from-to)2127-2131
Number of pages4
JournalSynlett
Issue number14
DOIs
Publication statusPublished - 22 Aug 2008

Keywords

  • electron donor
  • pyridinylidene
  • reduction
  • 4-DMAP

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