Photocatalyzed/Base-Mediated Defluorinative Three-ComponentCascade Cyclization: Access to Monofluorocyclohexenes and 6‑Fluoro-1,2,3,4-tetrahydropyridines

A three-component cascade cyclization of α-CF<sub>3</sub> alkenes, electron-rich alkenes, and dimethyl esters or sulfonamides via a dual C–F bond cleavage process is described. This methodology provides a general and efficient strategy to access monofluorocyclohexenes and 6-fluoro-1,2,3,4-tetrahydropyridines by switching the bifunctional reagents (dimethyl esters or sulfonamides), which are valuable building blocks in synthetic chemistry and the pharmaceutical industries. The reaction mechanism and the synthetic applications of the products have been demonstrated.

Publication Details

Journal
Figshare
Published
2025-03-19
DOI
https://doi.org/10.1021/acs.orglett.5c00675.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Photocatalyzed/Base-Mediated Defluorinative Three-ComponentCascade Cyclization: Access to Monofluorocyclohexenes and 6‑Fluoro-1,2,3,4-tetrahydropyridines

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Fluorine in Organic Chemistry
article

Photocatalyzed/Base-Mediated Defluorinative Three-ComponentCascade Cyclization: Access to Monofluorocyclohexenes and 6‑Fluoro-1,2,3,4-tetrahydropyridines

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Abstract

A three-component cascade cyclization of α-CF<sub>3</sub> alkenes, electron-rich alkenes, and dimethyl esters or sulfonamides via a dual C–F bond cleavage process is described. This methodology provides a general and efficient strategy to access monofluorocyclohexenes and 6-fluoro-1,2,3,4-tetrahydropyridines by switching the bifunctional reagents (dimethyl esters or sulfonamides), which are valuable building blocks in synthetic chemistry and the pharmaceutical industries. The reaction mechanism and the synthetic applications of the products have been demonstrated.

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Fluorine in Organic Chemistry
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Photocatalyzed/Base-Mediated Defluorinative Three-ComponentCascade Cyclization: Access to Monofluorocyclohexenes and 6‑Fluoro-1,2,3,4-tetrahydropyridines · Figshare (2025) | TGRS Research Map | TGRS