Visible-Light-Induced Trifluoromethyloximation of Alkenes with Sodium Nitrite as Oxime Source

A visible-light-induced, transition-metal- and photosensitizer-free three-component trifluoromethyloximation of alkenes is described herein. This established visible-light-driven difunctionalization process enables the straightforward and productive preparation of a diverse array of α-CF<sub>3</sub> ketoximes with high regioselectivity. The strategy employs commercially abundant and robust alkenes as starting materials, economical CF<sub>3</sub>SO<sub>2</sub>Cl as the trifluoromethylating agent, and NaNO<sub>2</sub> as the nitrosyl source, operating without transition-metal catalysts or external photosensitizers. This approach demonstrates broad functional group compatibility, high selectivity, mild reaction conditions, and excellent practicality.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-09
DOI
https://doi.org/10.1021/acs.joc.5c02372
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Visible-Light-Induced Trifluoromethyloximation of Alkenes with Sodium Nitrite as Oxime Source

Huiying Zeng, Renqin Zhan, Yong Jiang, Xiaoting Zou et al.
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Visible-Light-Induced Trifluoromethyloximation of Alkenes with Sodium Nitrite as Oxime Source

Huiying Zeng, Renqin Zhan, Yong Jiang, Xiaoting Zou, Xinlong Han
article en

Abstract

A visible-light-induced, transition-metal- and photosensitizer-free three-component trifluoromethyloximation of alkenes is described herein. This established visible-light-driven difunctionalization process enables the straightforward and productive preparation of a diverse array of α-CF<sub>3</sub> ketoximes with high regioselectivity. The strategy employs commercially abundant and robust alkenes as starting materials, economical CF<sub>3</sub>SO<sub>2</sub>Cl as the trifluoromethylating agent, and NaNO<sub>2</sub> as the nitrosyl source, operating without transition-metal catalysts or external photosensitizers. This approach demonstrates broad functional group compatibility, high selectivity, mild reaction conditions, and excellent practicality.

The Journal of Organic ChemistryVol. 90(50)
State Key Laboratory of Chemical Engineering (CN), Lanzhou University (CN)
Openalex Percentile: Top 68%
Fluorine in Organic Chemistry
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