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DOI: 10.1055/s-2008-1078242
One-Pot Reduction of Aryl Iodides Using 4-DMAP Methiodide Salt
Publikationsverlauf
Publikationsdatum:
31. Juli 2008 (online)
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.
Key words
electron donor - pyridinylidene - reduction - 4-DMAP
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