Pd-Catalyzed Aryl C–H Imidation with Arene as the Limiting Reagent
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CitationBoursalian, Gregory B., Ming-Yu Ngai, Katarzyna N. Hojczyk, and Tobias Ritter. 2013. Pd-Catalyzed Aryl C–H Imidation with Arene as the Limiting Reagent. Journal of the American Chemical Society 135, no. 36: 13278–13281.
AbstractAn 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.
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