2-(2-Pyridyl)ethylsilyl Group as a New Class of Electroauxiliary. Fine Tuning of the Electron Transfer Driven Reactions by the Dynamic Coordination to Silicon

The introduction of 2-(2-pyridyl)ethyl group on silicon decreases the oxidation potentials of silyl-substituted heteroatom compounds. The molecular orbital calculations indicate that this effect is attributed to the dynamic coordination of the pyridyl group to silicon in the cation radical intermediate. Such coordination also facilitates the selective C-Si bond cleavage.