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

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

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The preparation of medium-sized benzo[b]azocines has always been challenging because of inher-ently 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 ex-periments and cyclic voltammetry measurements,which elucidate the radical pathway.Finally,density functional theory calculations further rationalize the rate-determining step and the unique chemoselec-tivity observed in this transformation.

Medium-sized N-heterocyclesElectrocatalysisRadicalMechanistic insightsSelenylation

Zhichuan Wang、Xin Wang、Quanxin Li、Shaofei Ni、Dongyang Zhao、Shubin Yang、Ge Qiu、Kai Sun

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College of Chemistry and Chemical Engineering,Yantai University,Yantai 264005,China

Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province,Shantou University,Shantou 515063,China

Aix Marseille Univ.,CNRS,Centrale Marseille,iSm2,Marseille,France

国家自然科学基金Qingchuang Technology Support Program of University in Shandong ProvinceSTU Scientific Research Foundation for Talents

218010072021KJ066NTF20022

2024

中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
年,卷(期):2024.35(2)
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