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Pd-Catalyzed Aryl C–H Imidation with Arene as the Limiting Reagent

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posted on 18.02.2016, 22:14 by Gregory B. Boursalian, Ming-Yu Ngai, Katarzyna N. Hojczyk, Tobias Ritter
An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzene­sulfon­imide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C–H bond functionalization occurs subsequently at a high oxidation state of the catalyst.