Redox- and light-switchable N-heterocyclic carbenes: a "soup-to-nuts'' course on contemporary structure-activity relationships

Switchable catalysts respond to various types of stimuli in a manner that results in distinct structural or electronic changes. When each state exhibits a different activity, selectivity, or solubility, the corresponding catalyst may be used to control chemical reactions in a temporally-or spatially-resolved fashion. N-Heterocyclic carbenes (NHCs) are versatile scaffolds for building switchable catalysts and many examples that respond to changes in electrochemical potential or light have been introduced. Such types of switchable NHCs will be described in this Feature Article. The accompanying discussions include design considerations, characterization methodology, quantification of the underlying switching phenomena, and utility in catalytic applications. Challenges for the field as well as perspectives on potential opportunities for future development are also provided.