Amination of Nitro-Substituted Heteroarenes by Nucleophilic Substitution of Hydrogen

13 September 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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). DFT calculations and mechanistic studies support a dianion pathway with oxidation by molecular oxygen as the rate-limiting step.

Keywords

Substitution reactions
SNH
SNAr
Oxidative Nucleophilic Substitution of Hydrogen
ONSH

Supplementary materials

Title
Description
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Title
ESI: Amination of Nitro-Substituted Heteroarenes by Nucleophilic Substitution of Hydrogen
Description
Supporting information
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