Inspired by the role of N-heterocyclic carbenes (NHCs) in natural enzymatic processes, chemists have harnessed the umpolung (polarity reversal) reactivity of these Lewis basic species over the past few decades to construct key chemical bonds. While NHCs continue to play a role in two-electron transformations, their unique redox properties enable a variety of useful, stabilized radical species to be accessed via single-electron oxidation or reduction. As a result, their utility in synthesis has grown rapidly concurrent with the revival of radical chemistry, highlighted by their extensive use as reactive single-electron species in recent years.
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