Copper(I)-Catalyzed Synthesis of 1-Amino-1,3-diene Derivatives through a Formal 1,3-Amino Migration Process
Related Experiment Video
Updated: Sep 18, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Junwei Li1, Shuangshuang Liu1, Tiantian Zhang1
1College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China.
Abstract:
We present a highly efficient method utilizing a CuBr/DTBP (di-tert-butyl peroxide) catalyst system for the synthesis of 1-amino-1,3-diene derivatives from propargylamines and activated methylene compounds. This transformation efficiently assembles a wide range of substrates with good functional group tolerance and high atomic efficiency. Mechanistic investigations reveal that this reaction proceeds through a copper-catalyzed C-C bond formation followed by a formal 1,3-amino group migration. Notably, the C-N bond activation facilitated by cross-dehydrogenative coupling is identified as a crucial step that ensures the smooth progression of the reaction.
More Related Videos
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
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...
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: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
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...