Copper-Catalyzed One-Step Formation of Four C-N Bonds toward Polyfunctionalized Triazoles via Multicomponent Reaction
Xuelun Duan1, Nan Zheng1, Gongbo Liu1
1State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Science, Department of Polymer Science & Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China.
Abstract:
A novel four-component reaction of alkynes, amines, azides, and 2H-azirines has been developed for the first time by the efficient formation of four C-N bonds in one step under mild conditions, rapidly preparing polyfunctionalized triazoles with molecular diversity involving three different intermediates of copper-acetylide, copper-allenylidene, and copper-vinyl nitrene. Propargylic ester is disclosed as a "three-in-one" building block possessing triplicate cycloaddition and nucleophilic and electrophilic properties, which could enable such a four-component transformation by high yields, broad substrate scope, and functionalization.
More Related Videos
Related Concept Videos
Cycloaddition Reactions: Overview
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...


![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)