Abstract
Magnesium-promoted reductive silylation of 2- and 4-vinylpyridines with chlorotrialkylsilanes in N-methylpyrrolidinone at room temperature led to the selective formation of a variety of the corresponding β-mono-silylated compounds at the terminal carbon atom in good to excellent yields, whereas silylation of 3-vinylpyridine under the same reduction conditions failed to give a complex mixture of silylated compounds. The difference of the results between 2- or 4-vinylpyridines and 3-vinylpyridine is attributed to that of the stabilizing effect to reaction intermediates by the resonance with the nitrogen atom of pyridine.
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