Recent Advances in Gold-Catalyzed Transformations of Vinyldiazo Reagents

Abstract

Since their discovery in 2011, gold-catalyzed transformations of vinyldiazo compounds have become an important synthetic tool, enabling the identification of new reaction patterns that have greatly expanded the versatility of these reagents. In this short review, we showcase the most relevant advances that have been made in this exciting area of research.

1 Introduction

2 Gold-Catalyzed Transformations of Vinyldiazo Compounds Involving Metal Carbene Intermediates

2.1 Liu’s Seminal Work: Vinylogous Reactivity of Au(I) Vinyl Carbenes

2.2 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Alkenes

2.3 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Alkynes

2.4 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Allenes

2.5 Gold-Catalyzed Reactions of Vinyldiazo Reagents with Aromatic Compounds

2.6 Gold-Catalyzed Reactions of Vinyldiazo Compounds with Nitriles

2.7 Gold-Catalyzed Diazo Cross-Couplings

3 Gold-Catalyzed Transformations of Vinyldiazo Compounds That Do Not Involve Initial Dinitrogen Extrusion

3.1 Gold-Catalyzed Formal [n+2] Cycloaddition Reactions through the Vinyl Moiety of Vinyldiazo Compounds

3.2 Gold-Catalyzed Transformations of Vinyldiazo Compounds Involving Initial Activation of the Non-Diazo Reagent

4 Conclusions

Key words

vinyldiazo compounds - gold - carbenes - cyclization - C–H functionalization - regioselectivity

Publication History

Received: 10 May 2024

Accepted after revision: 11 June 2024

Accepted Manuscript online:
11 June 2024

Article published online:
04 July 2024

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