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用于二苯并硒吩合成的位点选择性电化学分子内C(sp)-H硒化反应

Site-Selective Electrochemical Intramolecular C(sp)-H Selenylation for Dibenzoselenophene Synthesis.

作者信息

Karmakar Indrajit, Jian Yi-Xuan, Cheng Wan-Lin, Bai Rekha, Chen Yu-Hsuan, Lee Chin-Fa

机构信息

Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan, R.O.C.

i-Center for Advanced Science and Technology (iCAST), National Chung Hsing University, Taichung 402, Taiwan, R.O.C.

出版信息

J Org Chem. 2025 Aug 29;90(34):12205-12215. doi: 10.1021/acs.joc.5c01600. Epub 2025 Aug 18.

DOI:10.1021/acs.joc.5c01600
PMID:40825176
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12400415/
Abstract

We report a robust and eco-conscious electrosynthetic protocol for efficiently constructing structurally diverse and biologically relevant dibenzoselenophenes. This transformation proceeds electrochemical intramolecular C-H activation of bis(biaryl) diselenides, employing LiClO as a green electrolyte and tetrabutylammonium bromide as an additive, conducted in DMSO at 70 °C under a constant current of 10 mA using Pt/Pt electrodes. The newly developed method offers several notable advantages, including mild and energy-efficient conditions, transition-metal-free catalysis, short reaction times, high to excellent yields, broad substrate tolerance, scalability to gram-scale synthesis, operational simplicity, and environmental friendliness.

摘要

我们报道了一种稳健且注重生态的电合成方法，用于高效构建结构多样且具有生物学相关性的二苯并硒吩。该转化过程通过双（联芳基）二硒醚的电化学分子内C-H活化反应实现，使用LiClO作为绿色电解质，四丁基溴化铵作为添加剂，在DMSO中于70°C、10 mA恒流下使用Pt/Pt电极进行反应。新开发的方法具有几个显著优点，包括温和且节能的条件、无过渡金属催化、反应时间短、产率高至优异、底物耐受性广、可扩展至克级规模合成、操作简便以及环境友好性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0c9/12400415/c778e022e94e/jo5c01600_0008.jpg
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