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

Boursalian, Gregory B.; Ngai, Ming-Yu; Hojczyk, Katarzyna N; Ritter, Tobias

doi:10.1021/ja4064926

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

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Boursalian, G. B., Ngai, M.-Y., Hojczyk, K. N., & Ritter, T. (2013). Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent. Journal of the American Chemical Society, 135(36), 13278-13281. doi: 10.1021/ja4064926.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-43C2-9

Abstract

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.