An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions

Abstract

N-Tosylhydrazones have had widespread application in organic synthesis for more than a half century. In most of cases, N-tosylhydrazones, as masked diazo compounds, have been generally used in a series of important carbon–carbon and carbon–heteroatom bond-forming reactions. This review provides an update on progress in diverse coupling reactions of N-tosylhydrazones since 2012. The examples selected are mainly categorized by metal-catalyzed and metal-free systems, wherein four main types of transformations including insertion, olefination, alkynylation, and cyclization are discussed for each system.

1 Introduction

2 Transition-Metal-Catalyzed Coupling Reactions

3 Metal-Free Coupling Reactions

4 Conclusion and Outlook

Key words

N-tosylhydrazones - coupling reaction - transition-metal catalysis - metal-free catalysis - metal–carbenes - migratory insertion - cascade reaction

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