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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