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Reductive Silylation Using a Bis‐silylated Diaza‐2,5‐cyclohexadiene
Author(s) -
Beagan Daniel M.,
Huerfano I. J.,
Polezhaev Alexander V.,
Caulton Kenneth G.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900879
Subject(s) - silylation , deoxygenation , trimethylsilyl , reagent , chemistry , reductive elimination , solvent , redox , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
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.