Stable Organic Radicals Derived from N-Heterocyclic Carbenes.

Over the past decade, numerous stable organic and main-group radicals have been synthesized from N-heterocyclic carbenes (NHCs). The structure of NHCs, in particular, offers electronic stabilization that helps to delocalize the unpaired electron over the molecule. In addition, the sterically bulky substituents of NHCs protect the radical center to prevent detrimental reactions such as dimerization. These advantages enable the straightforward synthesis and characterization of various interesting organic radicals starting from NHCs, which are, these days, widely available. NHCs have enabled the structural characterization of various organic radicals over the past decade, including α-carbonyl, propargyl, oxyallyl, and triazenyl radicals as notable examples. This minireview summarizes the advances in this field, mainly focusing on the preparation and stability as well as the properties and applications of NHC-derived organic radicals.