One-Pot Reduction of Aryl Iodides Using 4-DMAP Methiodide Salt

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...

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Bibliographic Details
Published in:Synlett 2008-08, Vol.2008 (14), p.2127-2131
Main Authors: Garnier, Jean, Murphy, John A., Zhou, Sheng-Ze, Turner, Andrew T.
Format: Article
Language:English
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2008-1078242