Citation: Zhichuan Wang, Xin Wang, Quanxin Li, Shaofei Ni, Dongyang Zhao, Shubin Yang, Ge Qiu, Kai Sun. Chemoselective electrochemical seleno-cyclization of dienes to medium-sized benzo[b]azocines[J]. Chinese Chemical Letters, ;2024, 35(2): 109058. doi: 10.1016/j.cclet.2023.109058 shu

Chemoselective electrochemical seleno-cyclization of dienes to medium-sized benzo[b]azocines

Zhichuan Wang ^a ,
Xin Wang ^a ,
Quanxin Li ^b ,
Shaofei Ni ^{b, *,} ,
Dongyang Zhao ^a ,
Shubin Yang ^a ,
Ge Qiu ^{a, c, *,} ,
Kai Sun ^{a, *,}

a.
College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
b.
Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou 515063, China
c.
Aix Marseille Univ., CNRS, Centrale Marseille, iSm2, Marseille, France

sfni@stu.edu.cn

gegeqiu@sina.com

sunk468@nenu.edu.cn

Received Date: 23 April 2023
Revised Date: 29 August 2023
Accepted Date: 5 September 2023
Available Online: 10 September 2023

Figures(9)

The preparation of medium-sized benzo[b]azocines has always been challenging because of inherently unfavorable enthalpy and entropy factors. This report presents a novel approach for accessing 8-membered seleno-benzo[b]azocines via electrochemically-driven seleno-cyclization. This method enables room-temperature preparation of various structurally diverse medium-sized seleno-benzo[b]azocines. The facile deselenation of the seleno-cyclization products to generate functionalized dienes is an additional benefit of this indispensable reaction. Mechanistic insights are presented based on radical inhibition experiments and cyclic voltammetry measurements, which elucidate the radical pathway. Finally, density functional theory calculations further rationalize the rate-determining step and the unique chemoselectivity observed in this transformation.
- Medium-sized N-heterocycles,
- Electrocatalysis,
- Radical,
- Mechanistic insights,
- Selenylation
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