Shen Lei, Zhang Xiaotong, Chen Shiyu, Yue Ling, Liang Kangjiang, Xia Chengfeng
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming 650500, China.
JACS Au. 2025 Jun 29;5(7):3417-3423. doi: 10.1021/jacsau.5c00470. eCollection 2025 Jul 28.
The direct photoexcitation of anions generated by deprotonation of C-H bonds under visible light has been less explored. Herein, we report that cyanohydrins can be photoexcited by visible light irradiation upon deprotonation. The photoexcited cyanohydrin anions demonstrate exceptional reducing capabilities, facilitating the single-electron transfer to aryl halides under mild conditions. The generated persistent cyanohydrin radicals serve as versatile acyl radical precursors for redox-neutral three-component acylarylation of olefins with a broad substrate scope. This study establishes cyanohydrin anions as a new class of photoactive species, offering a sustainable strategy for C-C bond formation without external oxidants or transition metals.
在可见光下，由C-H键去质子化产生的阴离子的直接光激发研究较少。在此，我们报道了氰醇在去质子化后可被可见光照射光激发。光激发的氰醇阴离子表现出卓越的还原能力，能在温和条件下促进向芳基卤化物的单电子转移。生成的持久性氰醇自由基作为通用的酰基自由基前体，可用于烯烃的氧化还原中性三组分酰基芳基化反应，底物范围广泛。本研究确立了氰醇阴离子作为一类新型光活性物种，为无需外部氧化剂或过渡金属的C-C键形成提供了一种可持续策略。
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