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Published on: September 8, 2016
Reductive Silylation Using a Bis-silylated Diaza-2,5-cyclohexadiene
Daniel M Beagan1, I J Huerfano1, Alexander V Polezhaev1
1Department of Chemistry, Indiana University, Bloomington, IN, 47405, USA.
Abstract:
1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene, 1, was tested as a reagent for the reductive silylation of various unsaturated functionalities, including N-heterocycles, quinones, and other redox-active moieties in addition to deoxygenation of main group oxides. Whereas most reactions tested are thermodynamically favorable, based on DFT calculations, a few do not occur, perhaps giving limited insight on the mechanism of this very attractive reductive process. Of note, reductive silylation reactions show a strong solvent dependence where a polar solvent facilitates conversions.
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