Synthesis of Aminated\nC‑3 Aryloylated Benzofuran,\nFuropyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne\nand <i>N</i>‑Aminopyridinium Salt in Visible Light

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

Publication Details

Journal
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Published
2024-12-20
DOI
https://doi.org/10.1021/acs.joc.4c02439.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Synthesis of Aminated\nC‑3 Aryloylated Benzofuran,\nFuropyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne\nand N‑Aminopyridinium Salt in Visible Light

Figshare
Catalytic C–H Functionalization Methods
article

Synthesis of Aminated\nC‑3 Aryloylated Benzofuran,\nFuropyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne\nand N‑Aminopyridinium Salt in Visible Light

article en

Abstract

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

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Catalytic C–H Functionalization Methods
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