Site-Selective Electrochemical Intramolecular C(sp<sup>2</sup>)–H Selenylation for Dibenzoselenophene Synthesis

We report a robust and eco-conscious electrosynthetic protocol for efficiently constructing structurally diverse and biologically relevant dibenzoselenophenes. This transformation proceeds <i>via</i> electrochemical intramolecular C-H activation of bis(biaryl) diselenides, employing LiClO<sub>4</sub> 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.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-08-18
DOI
https://doi.org/10.1021/acs.joc.5c01600
Citations
4
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
3.74

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article

Site-Selective Electrochemical Intramolecular C(sp2)–H Selenylation for Dibenzoselenophene Synthesis

Wan-Lin Cheng, Chin‐Fa Lee, Rekha Bai, Indrajit Karmakar et al.
4 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
3.74
article

Site-Selective Electrochemical Intramolecular C(sp2)–H Selenylation for Dibenzoselenophene Synthesis

Wan-Lin Cheng, Chin‐Fa Lee, Rekha Bai, Indrajit Karmakar, Yu‐Hsuan Chen, Yang Jian
article en
4 citations

Abstract

We report a robust and eco-conscious electrosynthetic protocol for efficiently constructing structurally diverse and biologically relevant dibenzoselenophenes. This transformation proceeds <i>via</i> electrochemical intramolecular C-H activation of bis(biaryl) diselenides, employing LiClO<sub>4</sub> 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.

The Journal of Organic ChemistryVol. 90(34)
National Chung Hsing University (TW), National Taipei University (TW)
Ministry of Education, India, National Chung-Hsing University, National Science and Technology Council, Science and Engineering Research Board
Openalex Percentile: Top 7%
Sulfur-Based Synthesis Techniques
3.74
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