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A simple and general method for arylation of carbon-hydrogen bonds in compounds containing directing groups has been developed. Anilides, benzylamines, benzoic acids, 2-aryl and alkylpyridines can be arylated in ortho-positions by using a combination of substrate, aryl iodide, silver acetate and catalytic palladium acetate. The use of a pyridine-containing removable auxiliary ligand allows the arylation of β-positions in carboxylic acid derivatives and γ-positions in amine derivatives. Non-activated sp3 carbon-hydrogen bonds are also reactive. A mechanistically distinct method for the alkenylation of anilides has also been developed.
Daugulis et al. (Fri,) studied this question.