Dedicated to Professor Emeritus Branko Stanovnik, University of Ljubljana, on the
occasion of his 80th birthday
Abstract
Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition
(CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless
on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained
overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC
reaction started to emerge as a promising supplement to the well-known CuAAC reaction.
The present review surveys primarily the literature on CuAIAC reaction since 2003.
Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected
examples of metal-free reactions, and related [3+3] and [3+4] cycloadditions of azomethine
imines are presented. All these experimental data indicate the viability of CuAIAC
in organic synthesis and the applicability in ‘click’ chemistry.
1 Introduction
2 Reactions with Acyclic Azomethine Imines
3 Reactions with C,N-Cyclic Azomethine Imines
4 Reactions with N,N-Cyclic Azomethine Imines
5 Reactions with C,N,N-Cyclic Azomethine Imines
6 The Mechanism of the CuAIAC Reaction
7 Conclusions and Outlook
Key words
azomethine imines - alkynes - cycloadditions - click chemistry - pyrazolines
