Oxidatively Induced C–H Activation at High Valent Nickel

Oxidatively Induced C–H Activation at High Valent Nickel

This communication describes a series of oxidatively induced intramolecular arene C–H activation reactions of NiII model complexes to yield NiIV σ-aryl products. These reactions proceed within 10 min at room temperature, which represents among the mildest conditions reported for C–H cleavage at a Ni...

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Veröffentlicht in:Journal of the American Chemical Society 2017-05, Vol.139 (17), p.6058-6061
Hauptverfasser: Chong, Eugene, Kampf, Jeff W, Ariafard, Alireza, Canty, Allan J, Sanford, Melanie S
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container_issue 17
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container_title Journal of the American Chemical Society
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creator Chong, Eugene
Kampf, Jeff W
Ariafard, Alireza
Canty, Allan J
Sanford, Melanie S
description This communication describes a series of oxidatively induced intramolecular arene C–H activation reactions of NiII model complexes to yield NiIV σ-aryl products. These reactions proceed within 10 min at room temperature, which represents among the mildest conditions reported for C–H cleavage at a Ni center. A combination of density functional theory and preliminary experimental mechanistic studies implicate a pathway involving initial 2e– oxidation of the NiII starting materials by the F+ transfer reagent N-fluoro-2,4,6-trimethylpyridinium triflate followed by triflate-assisted C–H cleavage at NiIV to yield the products.
doi_str_mv 10.1021/jacs.7b02387
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