Related Experiment Video
Updated: Jul 14, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-Catalyzed (4 + 3) Cycloadditions of Salicylimines and 1,4-Enynes: Access to Benzazepines
Zhongwei Ye1, Li Li2, Jiamei Zhou1
1College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, China.
Abstract:
Benzazepines represent a class of valuable nitrogen-containing heterocyclic compounds and widely applicable synthetic intermediates. Thus, the development of efficient and selective synthetic strategies for benzazepine construction via rational synthon design is of great research significance. Herein, we report the design of 1,4-enynes as novel trimethylenemethane (TMM) precursors and their application in palladium-catalyzed (4 + 3) cycloaddition reactions. This transformation proceeds efficiently at room temperature, affording a variety of benzazepine derivatives in good yields with excellent chemoselectivity. The practicality of the developed methodology is verified by gram-scale synthesis. Moreover, the obtained benzazepine products can be readily transformed into oxepine derivatives and triazole derivatives, and can undergo intramolecular cyclization under gold catalysis. This work demonstrates that bench-stable 1,4-enynes can serve as innovative precursors for palladium-catalyzed TMM-involved allylic cycloaddition reactions, and highlights their broad synthetic utility.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Cycloaddition Reactions: Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Nucleophilic Aromatic Substitution: Elimination–Addition
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene