Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates <i>via</i> energy transfer

Tang, Shuo; Liu, Jiupeng; Zhang, Min; Wang, Dan; Wang, Yong; Zhao, Jingjing; Li, Pan

doi:10.1039/d4qo00249k

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00249k

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Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates via energy transfer

Shuo Tang,

Jiupeng Liu,

Min Zhang

et al.

Abstract: A photochemical [2 + 2 + 1] radical annulation of 2-vinyloxy arylalkynes with bromomalonates has been developed. This protocol affords a metal-free, photocatalyst-free, oxidant-free and base-free approach to cyclopenta[b]benzofuran under...

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

Rajput,

Rajat,

Nitesh

et al. 2024

J. Org. Chem.

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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 Naminopyridinium 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.

show abstract

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

Rajput,

Rajat,

Nitesh

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

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Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates via energy transfer

Abstract: A photochemical [2 + 2 + 1] radical annulation of 2-vinyloxy arylalkynes with bromomalonates has been developed. This protocol affords a metal-free, photocatalyst-free, oxidant-free and base-free approach to cyclopenta[b]benzofuran under...

Cited by 1 publication

References 36 publications

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

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

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