1,2,3-triazolium compounds comprise one class of mesoionic carbenes (MICs), which are known to be powerful transition metal ligands as well as organocatalysts. While their two-electron chemistry has been well explored, our group recently discovered their ability to facilitate one-electron reduction chemistry. This was demonstrated by the organocatalytic arylacylation of alkenes via super electron donating MIC-derived Breslow Intermediates. The latter reduce iodoarenes to generate the corresponding aryl radical which then adds to an alkene, with subsequent addition to the oxidized Breslow Intermediate yielding the arylacylated alkene. Of note, this type of chemistry is less accessible for N-heterocyclic carbenes (NHCs), as Breslow Intermediates derived from NHCs have significantly less reducing redox potentials. This talk will explore the one-electron chemistry of 1,2,3-triazolium MICs and offer perspectives for future inquiry.

1,2,3-triazole-derived mesoionic carbenes as one-electron reductants

ACS Spring 2022

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