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Updated: Oct 10, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Reductively disilylated N-heterocycles as versatile organosilicon reagents
Padmini Sahoo1, Moumita Majumdar1
1Department of Chemistry, Indian Institute of Science Education and Research, Pune-411008, Maharashtra, India. moumitam@iiserpune.ac.in.
Abstract:
The reductively disilylated N-heterocyclic systems 1,4-bis(trimethylsilyl)-1-aza-2,5-cyclohexadiene (1Si), 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (2Si) and its methyl derivatives (3Si and 4Si), and 1,1'-bis(trimethylsilyl)-4,4'-bipyridinylidene (5Si) are proficient organosilicon reagents owing to their low first vertical ionization potentials and the heterophilicity of the polarized N-Si bonds. These have prompted their reactivity as two-electron reductants or reductive silylations. These reactions benefit from the concomitant rearomatization of the N-heterocycles and liberation of trimethylsilyl halides or (Me3Si)2O, which are mostly volatile or easily removable byproducts. In this perspective, we have discussed the utilization of these reductively disilylated N-heterocyclic systems as versatile reagents in the salt-free reduction of transition metals (A) and main-group halides (B), in organic transformations (C) and in materials syntheses (D).
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