Synthesis of Aminated C-3 Aryloylated Benzofuran, Furopyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne and N-Aminopyridinium Salt in Visible Light

2024/12/20 by Shruti Rajput, Rajat, Nitesh +3 · 14 citations
Chemistry · #Benzofuran #Benzothiophene #Catalysis #Catalytic C–H Functionalization Methods #Chemistry #Enyne #Indole test #Materials science #Medicinal chemistry #Organic chemistry #Radical Photochemical Reactions #Salt (chemistry) #Stereochemistry #Sulfur-Based Synthesis Techniques #Tandem #Thiophene #Visible spectrum

paper · doi:10.1021/acs.joc.4c02439

published in The Journal of Organic Chemistry 90(1), 493-502 (American Chemical Society)

openalex publication_date 2024/12/20 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

We report a visible-light-assisted tandem oxidative 5- exo -dig cyclization of 1,6-enynes for the synthesis of aminated C-3 aryloylated benzofuran, furopyridine, benzothiophene, and indole derivatives. The nitrogen-centered radical generated in situ from N -aminopyridinium salt initiates the consecutive formation of C–N, C–C, and C–O bonds. The methodology exhibits good functional group tolerance and regioselectivity, furnishing products in good to excellent yields at room temperature. Preliminary biological screening of synthesized molecules reveals their potential as anticancer agents.

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