Metal-free synthesis of 3-thiocyanatobenzothiophenes by eosin Y photoredox-catalyzed cascade radical annulation of 2-alkynylthioanisoles

TitleMetal-free synthesis of 3-thiocyanatobenzothiophenes by eosin Y photoredox-catalyzed cascade radical annulation of 2-alkynylthioanisoles
Publication TypeJournal Article
Year of Publication2018
AuthorsTambe, SD, Jadhav, MS, Rohokale, RS, Kshirsagar, UA
JournalEuropean Journal of Organic Chemistry
Issue35
Pagination 4867-4873
Date PublishedSEP
Type of ArticleArticle
Abstract

A convenient, efficient, metal-free synthesis of 3-thiocyanatobenzothiophenes has been developed that uses eosin Y in a visible-light-mediated photoredox-catalyzed anion oxidation of the ammonium salt of thiocyanate and proceeds through the cascade radical annulation of 2-alkynylthioanisole at room temperature. The present protocol requires visible light as a green energy source, an organic dye as the photocatalyst, and oxygen as a green oxidant to provide a mild route with a broad substrate scope for the formation of potentially bioactive 3-substituted benzothiophene derivatives in good yields.

DOI10.1002/ejoc.201800833
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.882

Divison category: 
Organic Chemistry

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