Related Experiment Video
Updated: May 16, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Direct Amination of Anilines Utilizing Dearomatized Phenolate Species
Shaofeng Wu1, Haitao Li1, Shicheng Dong2
1State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, College of Chemistry, Xinjiang University, Urumqi 830017, China.
Abstract:
Activation of the aryl C-N bond underpins critical challenges in modern organic synthesis. Herein, the direct amination of anilines is presented via hypervalent iodine-mediated transient dearomatized phenolate intermediates, enabling selective C(aryl)-NH2 bond cleavage under mild conditions. A library of bioactive p-alkylaminophenols is synthesized in up to 85% yields within 3 h. Being used in late-stage drug diversification and mechanistic studies, this protocol offers a modular platform for complex amine construction.
More Related Videos
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

