Reductive Silylation Using a Bis-silylated Diaza-2,5-cyclohexadiene |
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| Authors: | Daniel M Beagan I J Huerfano Dr Alexander V Polezhaev Dr Kenneth G Caulton |
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| Institution: | 1. Department of Chemistry, Indiana University, Bloomington, IN, 47405 USA
These authors contributed equally to this work.;2. Department of Chemistry, Indiana University, Bloomington, IN, 47405 USA |
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| 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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| Keywords: | density functional calculations dihydropyrazines nitrogen heterocycles reductive silylation silyl transfer |
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