Abstract The development of aryl alkyl sulfides as dichotomous electrophiles for site‐selective silylation via C−S bond cleavage has been achieved. Iron‐catalyzed selective cleavage of C(aryl)−S bonds can occur in the presence of β‐diketimine ligands, and the cleavage of C(alkyl)−S bonds can be achieved by t‐BuONa without the use of transition metals, resulting in the corresponding silylated products in moderate to excellent yields. Mechanistic studies suggest that Fe−Si species may undergo metathesis reactions during the cleavage of C(aryl)−S bonds, while silyl radicals are involved during the cleavage of C(alkyl)−S bonds.
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