1H-1,2,3-Triazol-5-ylidenes as Catalytic Organic Single-Electron Reductants,Journal of the American Chemical Society

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1H-1,2,3-Triazol-5-ylidenes as Catalytic Organic Single-Electron Reductants
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-01-22 , DOI: 10.1021/jacs.3c14360
Mehdi Abdellaoui ₁ , Kai Oppel ₁ , Adam Vianna ₁ , Michele Soleilhavoup ₁ , Xiaoyu Yan ₂ , Mohand Melaimi ₁ , Guy Bertrand ₁

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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.

中文翻译：

1H-1,2,3-三唑-5-亚基作为催化有机单电子还原剂

大多数已知的单电子还原剂是以化学计量使用的金属基试剂，或者是有机物质和光催化剂的组合。在这里，我们报道了 1 H -1,2,3-triazol-5-ylidenes 不仅可以作为化学计量的单电子供体，而且可以作为催化有机还原剂，而不需要光催化剂。作为概念证明，我们研究了醌的还原，醌是参与各种生物和工业过程的众所周知的电子传送体。这项工作还为双（三唑）碳酸盐加合物的形成提供了实验证据，该加合物充当催化循环的静止状态和卡宾储存库。

更新日期：2024-01-22

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