Vinyldiazo Reagents and Metal Catalysts: A Versatile Toolkit for Heterocycle and Carbocycle Construction

Over the past decade, vinyldiazo compounds have provided mild, efficient, and highly selective methods for the construction of heterocycles and carbocycles. Dinitrogen extrusion with suitable catalysts provides the carbon framework for [3+n] cycloaddition with a large variety of dipolarophiles. This minireview, covering the latest achievements in the field of metalcatalyzed cyclization reactions with vinyldiazo reagents, focuses on reagent- or catalyst-dependent chemodivergence: different vinyldiazo reagents or metal catalysts direct reactions to different cyclization pathways that give different reaction outcomes. Accordingly, metal-catalyzed cyclization reactions of vinyldiazo compounds with nitrosoarenes, nitrones, indoles, and other diazo compounds are chosen to showcase the controllable versatility of the combination of vinyldiazo compounds with nitrosoarenes, nitrones, indoles, and other diazo compounds are chosen to showcase the controllable versatility of the combination of vinyldiazo reagents and metal catalysts.