Electrochemically Promoted Trifluoromethylation/Cyclization for the Synthesis of Isoxazoles and Phosphoramide Compounds Bearing Trifluoromethyl

An electrochemically promoted protocol for the synthesis of (4-trifluoromethyl)isoxazoles has been successfully developed through the oxidative cyclization reaction of 2-alkyn-1-one <i>O</i>-methyloximes with CF<sub>3</sub>SO<sub>2</sub>Na. This newly developed protocol exhibits higher step economy and higher atom economy compared to existing methods. Additionally, the electrochemical cyclization reaction of <i>N-</i>(diphenylphosphoryl)acrylamides with CF<sub>3</sub>SO<sub>2</sub>Na has also been achieved, yielding a series of unexplored trifluoromethyl phosphoramide compounds without the need for additional catalysts or external oxidants. This method provides an efficient and sustainable approach to obtain various isoxazoles and nitrogen-phosphorus heterocycles bearing a CF<sub>3</sub> moiety.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-29
DOI
https://doi.org/10.1021/acs.joc.5c02139
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.58
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article

Electrochemically Promoted Trifluoromethylation/Cyclization for the Synthesis of Isoxazoles and Phosphoramide Compounds Bearing Trifluoromethyl

Li Tang, Xinyu Tang, Mu‐Xue He, Yi Wu et al.
2 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
1.58
article

Electrochemically Promoted Trifluoromethylation/Cyclization for the Synthesis of Isoxazoles and Phosphoramide Compounds Bearing Trifluoromethyl

Li Tang, Xinyu Tang, Mu‐Xue He, Yi Wu, Zu‐Yu Mo, Hang Liu
article en
2 citations

Abstract

An electrochemically promoted protocol for the synthesis of (4-trifluoromethyl)isoxazoles has been successfully developed through the oxidative cyclization reaction of 2-alkyn-1-one <i>O</i>-methyloximes with CF<sub>3</sub>SO<sub>2</sub>Na. This newly developed protocol exhibits higher step economy and higher atom economy compared to existing methods. Additionally, the electrochemical cyclization reaction of <i>N-</i>(diphenylphosphoryl)acrylamides with CF<sub>3</sub>SO<sub>2</sub>Na has also been achieved, yielding a series of unexplored trifluoromethyl phosphoramide compounds without the need for additional catalysts or external oxidants. This method provides an efficient and sustainable approach to obtain various isoxazoles and nitrogen-phosphorus heterocycles bearing a CF<sub>3</sub> moiety.

The Journal of Organic ChemistryVol. 90(44)
Guangxi University (CN), Guilin Medical University (CN)
Openalex Percentile: Top 14%
Fluorine in Organic Chemistry
1.58
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