The [3 + 3] Cycloaddition Reaction of Trifluoromethyl Alkenes with <i>N</i> -Substituted Pyrrole-2-Carboxaldehydes: Synthesis of Fluorinated 4 <i>H</i> -Pyran Derivatives

A base-promoted [3 + 3] annulation of trifluoromethyl alkenes with N -substituted pyrrole-2-carboxaldehydes has been developed for the synthesis of fluorinated 4 H -pyran derivatives. This reaction involves the consecutive cleavage of C–F bonds in the trifluoromethyl and the formation of new chemical bonds without the use of a catalyst. Additionally, this methodology features mild reaction conditions and a good functional group tolerance.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-06-28
DOI
https://doi.org/10.1021/acs.joc.6c00953
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

The [3 + 3] Cycloaddition Reaction of Trifluoromethyl Alkenes with N -Substituted Pyrrole-2-Carboxaldehydes: Synthesis of Fluorinated 4 H -Pyran Derivatives

Chun Cai, Ying Liu
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

The [3 + 3] Cycloaddition Reaction of Trifluoromethyl Alkenes with N -Substituted Pyrrole-2-Carboxaldehydes: Synthesis of Fluorinated 4 H -Pyran Derivatives

Chun Cai, Ying Liu
article en

Abstract

A base-promoted [3 + 3] annulation of trifluoromethyl alkenes with N -substituted pyrrole-2-carboxaldehydes has been developed for the synthesis of fluorinated 4 H -pyran derivatives. This reaction involves the consecutive cleavage of C–F bonds in the trifluoromethyl and the formation of new chemical bonds without the use of a catalyst. Additionally, this methodology features mild reaction conditions and a good functional group tolerance.

The Journal of Organic Chemistry
Nanjing University of Science and Technology (CN)
Clean water and sanitation
Openalex Percentile: Top 9%
Fluorine in Organic Chemistry
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