Palladium-Catalyzed Direct Ortho C-H Arylation of 2-Arylpyridine Derivatives with Aryltrimethoxysilane

A Pd(OAc)(2)-catalyzed cross-coupling reaction between 2-arylpyridine and aryltrimethoxysilane in the presence of AgF and BQ in 1,4-dioxane was studied. After various reaction parameters (catalyst, oxidant, additive, solvent and reaction temperature) were examined, the optimal conditions for the reaction were identified. The synthesis is compatible to aryltrimethoxysilane with both electron-withdrawing and electron-donating groups on the aryl moiety with moderate yields. The kinetic isotope effect (k(H)/k(D)) for the C-H bond activation was provided.