Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Dedicated to Professor Emeritus Branko Stanovnik, University of Ljubljana, on the occasion of his 80^th 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

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