Citation: Ting Zou, Yishu He, Rui Liu, Yihao Zhang, Siping Wei, Ji Lu, Jun Wang, Lin Wang, Qiang Fu, Dong Yi. Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated NO/CC bond cleavages and sequential radical-radical coupling[J]. Chinese Chemical Letters, ;2023, 34(5): 107822. doi: 10.1016/j.cclet.2022.107822 shu

Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated NO/CC bond cleavages and sequential radical-radical coupling

Ting Zou ^{a, 1} ,
Yishu He ^{a, 1} ,
Rui Liu ^a ,
Yihao Zhang ^a ,
Siping Wei ^{a, c, *,} ,
Ji Lu ^a ,
Jun Wang ^a ,
Lin Wang ^a ,
Qiang Fu ^{a, **,} ,
Dong Yi ^{a, b, *,}

a.
Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou 646000, China
b.
Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province, Luzhou 646000, China
c.
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China

^**

swei1225@swmu.edu.cn

fuqiang@swmu.edu.cn

yidong@swmu.edu.cn

Received Date: 25 June 2022
Revised Date: 1 September 2022
Accepted Date: 13 September 2022
Available Online: 15 September 2022

Figures(7)

A novel photoredox-neutral ring-opening pyridylation of non-prefunctionalized cyclic oximes has been accomplished through phosphoranyl radical-mediated NO/CC 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.
- Pyridylation,
- Cyclic oxime,
- Phosphoranyl radical,
- Photoredox-neutral,
- Radical-radical coupling
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