Journal
ORGANIC LETTERS
Volume 24, Issue 41, Pages 7643-7648Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03133
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An open-air method for the direct amination of nitro(hetero)arenes without transition metals is introduced. It involves the substitution of an aromatic C-H bond through oxidative nucleophilic aromatic substitution of hydrogen (ONSH). Theoretical calculations and mechanistic studies indicate a dianion pathway with oxidation by molecular oxygen as the rate-limiting step.
An open-air method for the transition metal-free direct amination of nitro(hetero)arenes by anilines is disclosed. In this methodology, an aromatic C-H bond is substituted via oxidative nucleophilic aromatic substitution of hydrogen (ONSH). Density functional theory calculations and mechanistic studies support a dianion pathway with oxidation by molecular oxygen as the rate-limiting step.
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