Citation: Jun-Long Li, Si-Lin Yang, Qing-Song Dai, Hua Huang, Lu Jiang, Qing-Zhu Li, Qi-Wei Wang, Xiang Zhang, Bo Han. Modular synthesis of 1,4-diketones through regioselective bis-acylation of olefins by merging NHC and photoredox catalysis[J]. Chinese Chemical Letters, ;2023, 34(11): 108271. doi: 10.1016/j.cclet.2023.108271 shu

Modular synthesis of 1,4-diketones through regioselective bis-acylation of olefins by merging NHC and photoredox catalysis

Jun-Long Li ^a ,
Si-Lin Yang ^a ,
Qing-Song Dai ^a ,
Hua Huang ^b ,
Lu Jiang ^a ,
Qing-Zhu Li ^a ,
Qi-Wei Wang ^a ,
Xiang Zhang ^{a, *,} ,
Bo Han ^{a, b, *,}

a.
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China
b.
State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China

XZhang_CDU@hotmail.com

hanbo@cdutcm.edu.cn

Received Date: 13 November 2022
Revised Date: 16 February 2023
Accepted Date: 23 February 2023
Available Online: 2 March 2023

Figures(6)

Efficient and modular synthesis of structurally diverse 1,4-diketones from readily available building blocks represents an essential but challenging task in organic chemistry. Herein, we report a multi-component, regioselective bis-acylation of olefins by merging NHC organocatalysis and photoredox catalysis. With this protocol, a broad range of 1,4-diketones could be rapidly assembled using bench-stable feedstock materials. The robustness of this method was further evaluated by sensitivity screening, and good reproductivity was observed. Moreover, the diketone products could be readily converted into functionalized heterocycles, such as multi-substituted furan, pyrrole, and pyridazine. Mechanistic investigations shed light on the NHC and photoredox dual catalytic radical reaction mechanism.
- NHC organocatalysis,
- Photoredox catalysis,
- Radical bis-acylation,
- Multi-component reaction,
- 1,4-Diketone synthesis
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