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- W2897465262 abstract "The direct amination of C–H bonds with ammonia is a challenge in synthetic chemistry. Herein, we present a copper-mediated approach that enables a chelation-assisted aromatic C–H bond amination using aqueous ammonia. A key strategy was to use soft low-valent Cu(I) species to avoid the strong coordination of ammonia. Mechanistic investigations suggest that the catalysis is initiated by a facile deprotonation of bound ammonia, and the C–N coupling is achieved by subsequent reductive elimination of the resultant copper–amido intermediate from a Cu(III) intermediate that is readily generated by disproportionation of low-valent copper analogues. This mechanistic postulate was supported by a preliminary kinetic isotope effect study and computations. This new chelation-assisted, copper-mediated C–H bond amination with aqueous ammonia was successfully applied to a broad range of substrates to deliver primary anilines. Moreover, the mild conditions required for this transformation allowed the reaction to operate even under substoichiometric conditions to enable a late-stage application for the preparation of pharmaceutical agents." @default.
- W2897465262 created "2018-10-26" @default.
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- W2897465262 date "2018-10-12" @default.
- W2897465262 modified "2023-10-16" @default.
- W2897465262 title "Copper-Mediated Amination of Aryl C–H Bonds with the Direct Use of Aqueous Ammonia via a Disproportionation Pathway" @default.
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- W2897465262 doi "https://doi.org/10.1021/jacs.8b08826" @default.
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