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

作     者：Zhichuan Wang Xin Wang Quanxin Li Shaofei Ni Dongyang Zhao Shubin Yang Ge Qiu Kai Sun Zhichuan Wang;Xin Wang;Quanxin Li;Shaofei Ni;Dongyang Zhao;Shubin Yang;Ge Qiu;Kai Sun

作者机构：College of Chemistry and Chemical EngineeringYantai UniversityYantai 264005China Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong ProvinceShantou UniversityShantou 515063China Aix Marseille Univ.CNRSCentrale MarseilleiSm2MarseilleFrance 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2024年第35卷第2期

页      面：431-435页

核心收录：

学科分类：081702[工学-化学工艺] 08[工学] 0817[工学-化学工程与技术] 0703[理学-化学] 

基　　金：supported by the National Natural Science Foundation of China(No.21801007) Qingchuang Technology Support Program of University in Shandong Province(No.2021KJ066) S.-F.Ni acknowledges funding from the STU Scientific Research Foundation for Talents(No.NTF20022). 

主　　题：Medium-sized n-heterocycles Electrocatalysis Radical Mechanistic insights Selenylation 

摘      要：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.