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
