Regioselective functionalization of unreactive carbon-hydrogen bonds

A simple and general method for arylation of carbon-bydrogen 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 beta-positions in carboxylic acid derivatives and gamma-positions in amine derivatives. Non-activated sp(3) carbon-hydrogen bonds are also reactive. A mechanistically distinct method for the alkenylation of anilides has also been developed. 1 Introduction 2 Concept Development and Initial Results 3 Expansion of Arylation Scope 4 Conclusion and Outlook