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.
LanguageEnglish
Pages2127-2131
Number of pages4
JournalSynlett
Issue number14
DOIs
Publication statusPublished - 22 Aug 2008

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Iodides
Salts
Anions
Electrons
Protons

Keywords

  • electron donor
  • pyridinylidene
  • reduction
  • 4-DMAP

Cite this

Garnier, J., Murphy, J. A., Zhou, S. Z., Turner, A. T., EPRSC (Funder), University of Strathclyde (Funder), & AstraZeneca (Funder) (2008). One-pot reduction of aryl iodides using 4-dmap methiodide salt. Synlett, (14), 2127-2131. https://doi.org/10.1055/s-2008-1078242
Garnier, J. ; Murphy, J.A. ; Zhou, S.Z. ; Turner, A.T. ; EPRSC (Funder) ; University of Strathclyde (Funder) ; AstraZeneca (Funder). / One-pot reduction of aryl iodides using 4-dmap methiodide salt. In: Synlett. 2008 ; No. 14. pp. 2127-2131.
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Garnier, J, Murphy, JA, Zhou, SZ, Turner, AT, EPRSC (Funder), University of Strathclyde (Funder) & AstraZeneca (Funder) 2008, 'One-pot reduction of aryl iodides using 4-dmap methiodide salt' Synlett, no. 14, pp. 2127-2131. https://doi.org/10.1055/s-2008-1078242

One-pot reduction of aryl iodides using 4-dmap methiodide salt. / Garnier, J.; Murphy, J.A.; Zhou, S.Z.; Turner, A.T.; EPRSC (Funder); University of Strathclyde (Funder); AstraZeneca (Funder).

In: Synlett, No. 14, 22.08.2008, p. 2127-2131.

Research output: Contribution to journalArticle

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AU - Garnier, J.

AU - Murphy, J.A.

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Garnier J, Murphy JA, Zhou SZ, Turner AT, EPRSC (Funder), University of Strathclyde (Funder) et al. One-pot reduction of aryl iodides using 4-dmap methiodide salt. Synlett. 2008 Aug 22;(14):2127-2131. https://doi.org/10.1055/s-2008-1078242