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Pd-catalyzed aryl C-H imidation with arene as the limiting reagent.

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.

SUBMITTER: Boursalian GB

PROVIDER: S-EPMC3817741 | biostudies-other | 2013 Sep

REPOSITORIES: biostudies-other

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Pd-catalyzed aryl C-H imidation with arene as the limiting reagent.

Boursalian Gregory B GB Ngai Ming-Yu MY Hojczyk Katarzyna N KN Ritter Tobias T

Journal of the American Chemical Society 20130903 36

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 ...[more]

PMID: 23998528

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