1H-1,2,3-Triazol-5-ylidenes as Catalytic Organic Single-Electron Reductants.

Most of the known single-electron reductants are either metal based reagents, used in a stoichiometric amount, or a combination of an organic species and a photocatalyst. Here we report that 1H-1,2,3-triazol-5-ylidenes act not only as stoichiometric one-electron donors but also as catalytic organic reducing agents, without the need of a photocatalyst. As a proof of concept, we studied the reduction of quinones, which are well-known electron conveyors that are involved in various biological and industrial processes. This work also provides experimental evidence for the formation of a bis(triazolium)carbonate adduct, which acts as the resting state of the catalytic cycle and as the carbene reservoir.

Citation

Mehdi Abdellaoui, Kai Oppel, Adam Vianna, Michele Soleilhavoup, Xiaoyu Yan, Mohand Melaimi, Guy Bertrand. 1H-1,2,3-Triazol-5-ylidenes as Catalytic Organic Single-Electron Reductants. Journal of the American Chemical Society. 2024 Feb 07;146(5):2933-2938

PMID: 38253007

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