Related Experiment Video
Updated: Dec 25, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Copper-Catalyzed Remote C(sp3)-H Amination of Carboxamides
Qing-Qiang Min1, Jia-Wen Yang1, Meng-Juan Pang1
1Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China.
Abstract:
Here we report a method for the site-selective intermolecular C(sp3)-H amination of carboxamides by merging transition-metal catalysis and the hydrogen atom transfer strategy. The reaction proceeds through a sequence of favorable single-electron transfer, 1,5-hydrogen atom transfer, and C-N cross-coupling steps, thus allowing access to a series of desired products. This reaction could accommodate a wide diversity of nitrogen nucleophiles as well as demonstrate excellent chemoselectivity and functional group compatibility.
Related Concept Videos
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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...
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...

