Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated NO/CC bond cleavages and sequential radical-radical coupling |
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Institution: | 1. Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou 646000, China;2. Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province, Luzhou 646000, China;3. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China |
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Abstract: | A novel photoredox-neutral ring-opening pyridylation of non-prefunctionalized cyclic oximes has been accomplished through phosphoranyl radical-mediated N O/C C bond cleavages followed by radical-radical coupling. This mild acid-, base-, and oxidant-free protocol provides highly site-selective and efficient access to distally pyridylated alkylnitriles, which could be scale-up synthesized and readily converted into skeletally diverse compounds. Notably, the oxidized ground-state photocatalyst generated via the SET oxidation of the highly reducing excited-state photocatalyst by cyanopyridines might initiate the following phosphoranyl radical-mediated deoxygenative process. |
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