Citation: Xinyu Wang, Shihong Wu, Yujing Zhong, Yingchun Wang, Yingming Pan, Haitao Tang. Electrochemically mediated decarboxylative acylation of N-nitrosoanilines with α-oxocarboxylic acids[J]. Chinese Chemical Letters, ;2023, 34(2): 107537. doi: 10.1016/j.cclet.2022.05.051 shu

Electrochemically mediated decarboxylative acylation of N-nitrosoanilines with α-oxocarboxylic acids

Xinyu Wang ^{a, 1} ,
Shihong Wu ^{a, 1} ,
Yujing Zhong ^a ,
Yingchun Wang ^b ,
Yingming Pan ^{a, b, *,} ,
Haitao Tang ^{a, *,}

a.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China
b.
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China

panym@mailbox.gxnu.edu.cn

httang@gxnu.edu.cn

Received Date: 27 March 2022
Revised Date: 10 May 2022
Accepted Date: 15 May 2022
Available Online: 19 May 2022

Figures(4)

An efficient palladium-catalyzed electrooxidation C–H acylation reaction of N-nitrosoanilines with α-oxocarboxylic acids was developed. The anodic oxidation of the Pd(Ⅱ) intermediate was found to be the key to complete the reaction. In this case, the N-nitroso group was observed to be an effective directing group for C–H activation reaction. Moreover, the synthetic transformation of derivatives of natural products (L-menthol, dehydroepiandrosterone, and pregnenolone) was successfully realized. Finally, flow electrochemical synthesis of some substrates was achieved.
- Eelectro-oxidation,
- C-H acylation,
- N-Nitrosoanilines,
- Flow electrochemical synthesis
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