Citation: Qinghong Zhang, Qiao Zhao, Xiaodi Wu, Li Wang, Kairui Shen, Yuchen Hua, Cheng Gao, Yu Zhang, Mei Peng, Kai Zhao. Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer[J]. Chinese Chemical Letters, ;2025, 36(2): 110167. doi: 10.1016/j.cclet.2024.110167 shu

Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer

Qinghong Zhang ^{a, 1} ,
Qiao Zhao ^{a, 1} ,
Xiaodi Wu ^a ,
Li Wang ^a ,
Kairui Shen ^a ,
Yuchen Hua ^a ,
Cheng Gao ^a ,
Yu Zhang ^b ,
Mei Peng ^d ,
Kai Zhao ^{a, c, *,}

a.
Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China
b.
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
c.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
d.
College of Pharmacy, Hengyang Medical School, University of South China, Hengyang 421001, China

ias_kzhao@njtech.edu.cn

Received Date: 10 April 2024
Revised Date: 13 June 2024
Accepted Date: 21 June 2024
Available Online: 22 June 2024

Figures(6)

Pyridyl-based ketones and 1, 6-diketones are both attractive and invaluable scaffolds which play pivotal roles in the construction and structural modification of a plethora of synthetically paramount natural products, pharmaceuticals, organic materials and fine chemicals. In this context, we herein demonstrate an unprecedented, robust and generally applicable synthetically strategy to deliver these two crucial ketone frameworks via visible-light-induced ring-opening coupling reactions of cycloalcohols with vinylazaarenes and enones, respectively. A plausible mechanism involves the selective β-C-C bond cleavage of cycloalcohols enabled by proton-coupled electron transfer and ensuing Giese-type addition followed by single electron reduction and protonation. The synthetic methodology exhibits broad substrate scope, excellent functional group compatibility as well as operational simplicity and environmental friendliness.
- Pyridyl-based ketone,
- 1, 6-Diketone,
- Proton-coupled electron transfer,
- C-C Bond cleavage,
- Ring-opening coupling
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