Versatile Electrochemical Synthesis of Selenylbenzo[ b]Furan Derivatives Through the Cyclization of 2-Alkynylphenols

Carlos V Doerner; Marcos R Scheide; Celso R Nicoleti; Daniele C Durigon; Vinícius D Idiarte; Martinho J A Sousa; Samuel R Mendes; Sumbal Saba; José S S Neto; Guilherme M Martins; Jamal Rafique; Antonio L Braga

doi:10.3389/fchem.2022.880099

Versatile Electrochemical Synthesis of Selenylbenzo[ b]Furan Derivatives Through the Cyclization of 2-Alkynylphenols

Front Chem. 2022 May 17:10:880099. doi: 10.3389/fchem.2022.880099. eCollection 2022.

Authors

Affiliations

¹ Departamento de Química, Universidade Federal de Santa Catarina-UFSC, Florianópolis, Brazil.
² Instituto de Química, Universidade Federal do Mato Grosso do Sul.-UFMS, Campo Grande, Brazil.
³ Departamento de Química, Universidade do Estado de Santa Catarina, Joinville, Brazil.
⁴ Instituto de Química, Universidade Federal de Goiás-UFG, Goiânia, Brazil.
⁵ Department of Chemical Sciences, Faculty of Science, University of Johannesburg, Doornfontein, South Africa.

Abstract

We report an electrochemical oxidative intramolecular cyclization reaction between 2-alkynylphenol derivatives and different diselenides species to generate a wide variety of substituted-benzo[b]furans. Driven by the galvanostatic electrolysis assembled in an undivided cell, it provided efficient transformation into oxidant-, base-, and metal-free conditions in an open system at room temperature. With satisfactory functional group compatibility, the products were obtained in good to excellent yields.

Keywords: diselenide; electrosynthesis; selenium; seleno-cyclization; selenylbenzo[b]furans.