Electrosynthesis of Functionalized Chromenes via Selenylation-Induced Alkynes Cyclization

Abstract An efficient electrochemical method for the synthesis of functionalized chromenes via selenylation-induced intramolecular cyclization of alkynes is described. Herein, selenylated chromenes are obtained in yields up to 96%, without the need for external oxidants using an undivided cell equipped with carbon electrodes under galvanostatic conditions. Mechanistic investigations support an anodic generation of electrophilic selenium species, followed by intramolecular cyclization. Furthermore, the method encompasses a versatile substrate scope, demonstrates efficiency on a gram scale, and is significantly improved by using continuous-flow conditions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-09-19
DOI
https://doi.org/10.1021/acs.joc.6c01733
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Electrosynthesis of Functionalized Chromenes via Selenylation-Induced Alkynes Cyclization

Kléber T. de Oliveira, Roberto G. S. Berlinck, Guilherme M. Martins, Pedro P. de Castro et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Electrosynthesis of Functionalized Chromenes via Selenylation-Induced Alkynes Cyclization

Kléber T. de Oliveira, Roberto G. S. Berlinck, Guilherme M. Martins, Pedro P. de Castro, João P. R. S. Ribeiro, Samuel R. Mendes, Felipe de Lucca, Manoella de Lima
article en

Abstract

Abstract An efficient electrochemical method for the synthesis of functionalized chromenes via selenylation-induced intramolecular cyclization of alkynes is described. Herein, selenylated chromenes are obtained in yields up to 96%, without the need for external oxidants using an undivided cell equipped with carbon electrodes under galvanostatic conditions. Mechanistic investigations support an anodic generation of electrophilic selenium species, followed by intramolecular cyclization. Furthermore, the method encompasses a versatile substrate scope, demonstrates efficiency on a gram scale, and is significantly improved by using continuous-flow conditions.

The Journal of Organic Chemistry
Universidade Federal de Juiz de Fora (BR), Universidade do Estado de Santa Catarina (BR), Universidade Federal de São Carlos (BR), Universidade de São Paulo (BR)
Openalex Percentile: Top 20%
Radical Photochemical Reactions
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Electrosynthesis of Functionalized Chromenes via Selenylation-Induced Alkynes Cyclization — Kléber T. de Oliveira, Roberto G. S. Berlinck, et al. · The Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS