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

Garnier, J. and Murphy, J.A. and Zhou, S.Z. and 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). pp. 2127-2131. ISSN 0936-5214

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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.