A palladium-catalyzed cyanation of aryl dimethylsulfonium
salts
using cheap, nontoxic, and bench-stable K4[Fe(CN)6]·3H2O as the cyanating reagent has been developed.
The reactions proceeded well under base-free conditions with various
sulfonium salts and provided aryl nitrile with yields of up to 92%.
Aryl sulfides can be transformed to aryl nitriles directly via a one-pot
process, and the protocol is scalable. Density functional theory calculations
were performed to investigate the reaction mechanism that involved
a catalytic cycle involving oxidative addition, ligand exchange, reductive
elimination, and regeneration to yield the product.
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