Visible Light-Induced\nOrganophotoredox-Catalyzed β‑Hydroxytrifluoromethylation\nof Unactivated Alkenes

Herein, we report a mild transition metal-free organophotoredox-catalyzed\napproach for β-hydroxytrifluoromethylation of unactivated alkenes\nusing CF<sub>3</sub>SO<sub>2</sub>Na and acridinium salt. The protocol\nis compatible with various mono-, di-, and trisubstituted aliphatic\nunactivated alkenes containing numerous functional groups and natural\nproduct derivatives. Further, the postsynthetic modifications of the\nsynthesized trifluoromethylated products have been demonstrated through\ncross-coupling and functional group interconversion reactions. The\nmethod proved to be scalable and it works smoothly under the direct\nexposure of sunlight. A plausible mechanism has been proposed based\non the fluorescence quenching experiment and cyclic voltammetry analysis.

Publication Details

Journal
Figshare
Published
2024-10-09
DOI
https://doi.org/10.1021/acs.joc.4c00967.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Visible Light-Induced\nOrganophotoredox-Catalyzed β‑Hydroxytrifluoromethylation\nof Unactivated Alkenes

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Fluorine in Organic Chemistry
article

Visible Light-Induced\nOrganophotoredox-Catalyzed β‑Hydroxytrifluoromethylation\nof Unactivated Alkenes

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Abstract

Herein, we report a mild transition metal-free organophotoredox-catalyzed\napproach for β-hydroxytrifluoromethylation of unactivated alkenes\nusing CF<sub>3</sub>SO<sub>2</sub>Na and acridinium salt. The protocol\nis compatible with various mono-, di-, and trisubstituted aliphatic\nunactivated alkenes containing numerous functional groups and natural\nproduct derivatives. Further, the postsynthetic modifications of the\nsynthesized trifluoromethylated products have been demonstrated through\ncross-coupling and functional group interconversion reactions. The\nmethod proved to be scalable and it works smoothly under the direct\nexposure of sunlight. A plausible mechanism has been proposed based\non the fluorescence quenching experiment and cyclic voltammetry analysis.

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Fluorine in Organic Chemistry
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