Transition Metal-catalyzed Reactions involving Isocyanides

Isocyanides are highly versatile reagents that have found widespread applications in organic, medicinal and combinatorial chemistry (e.g. multicomponent reactions, heterocycle synthesis and cycloadditions). Since isocyanides are isoelectronic with CO, they show similar reactivity towards transition metals and undergo the same fundamental transformations. However, their use in transition metal catalysis is much less explored. This is surprising considering the significant advantages of isocyanides. Isocyanides are easily handled liquids or solids and can therefore be used in stoichiometric quantities, while CO is a toxic gas typically used in excess and under high pressures. Most importantly, however, isocyanides have a diversity point, which makes them more flexible. Consequently, transition-metal catalyzed reactions utilizing isocyanide insertion offer tremendous opportunities for the synthesis of functional groups containing a nitrogen functionality. It is therefore not surprising that this type of chemistry has seen a surge of interest in the last years. This research is in collaboration with Prof. Orru from the Free University of Amsterdam.