Hypervalent iodine reagent mediated acetoxylation of N -protected anilines: A comparative analysis

An efficient alternative methodology for the selective functionalization of anilides has been developed through the synergistic combination of PIDA and copper(II) acetate monohydrate in acetic acid. A comparative analysis with previously reported methodologies has been carried out. The developed protocol offer a practical and effective alternative to conventional methods employing expensive or toxic heavy-metal catalysts, highlighting the versatility and cost-effectiveness of copper salts in C-H functionalization reactions. The methodology was operationally simple and proceeds under mild reaction conditions, affording ortho -functionalized products in good to excellent yields. The obtained results were found to be consistent with reported palladium and cobalt-mediated protocols, while differ from Lewis acid promoted methodologies. Additional advantages of this approach include shorter reaction times, high reaction efficiency, and a simplified work-up procedure that avoids chromatographic purification. A plausible reaction mechanism involving ortho -assisted metal chelation has also been proposed.