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通过芳炔与硫代奥酮类似物的多米诺反应构建八元环状二芳基硫醚及其反应机理的密度泛函理论研究

Construction of Eight-Membered Cyclic Diaryl Sulfides via Domino Reaction of Arynes with Thioaurone Analogues and DFT Study on the Reaction Mechanism.

作者信息

Ding Wenhuan, Yu Aimin, Zhang Lei, Meng Xiangtai

机构信息

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering , Tianjin University of Technology , Tianjin 300384 , P. R. China.

Tianjin Engineering Technology Center of Chemical Wastewater Source Reduction and Recycling, School of Science , Tianjin Chengjian University , Tianjin 300384 , P. R. China.

出版信息

Org Lett. 2019 Nov 15;21(22):9014-9018. doi: 10.1021/acs.orglett.9b03417. Epub 2019 Nov 5.

DOI:10.1021/acs.orglett.9b03417
PMID:31687828
Abstract

Eight-membered cyclic and [5,5]-bicyclic sulfides were synthesized via a domino reaction between thioaurone analogues and arynes. Density functional theory calculations were performed to elucidate the reaction mechanism, which involves the elementary steps of the [3 + 2] cycloaddition, 1,2-hydrogen shift, and C(sp)-S bond cleavage as well as the substituent effect.

摘要

通过硫代奥酮类似物与芳炔之间的多米诺反应合成了八元环状和[5,5] -双环硫化物。进行了密度泛函理论计算以阐明反应机理，该机理涉及[3 + 2]环加成、1,2-氢迁移、C(sp)-S键断裂等基本步骤以及取代基效应。

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