New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(sp³)–F Bond Cleavage

JACS Au, Journal Year: 2025, Volume and Issue: 5(2), P. 466 - 485

Published: Feb. 7, 2025

Fluorinated molecules are of paramount importance because their unique properties. As a result, the search for innovative approaches to synthesis this class compounds has been relentless over years. Among these, combination photocatalysis and organofluorine chemistry turned out be an effective partnership access unattainable fluorinated molecules. This Perspective provides overview recent advances in synthesizing via organophotoredox-catalyzed defluorination process from trifluoromethylated compounds. It encompasses preparation difluoromethylated (hetero)arenes, amides, esters as well gem-difluoroalkene derivatives using C(sp3)–F bond activation or β-fragmentation. will highlight remaining challenges discuss future research opportunities.

Language: Английский

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Photoinduced Iron-Catalyzed Decarboxylation/Isomerization of gem-Difluoroallyl Carboxylic Acid to Access Vinyl Difluoromethylene Units

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 28, 2025

Vinyl difluoromethylene units (−CF−) significantly enhance the bioactivity and physical chemical properties of compounds. Despite recent advances in introducing vinyl units, radical-mediated formation these motifs remains largely unexplored. A novel serial catalytic strategy for selective defluoroalkylation trifluoromethyl alkenes has been developed, utilizing photocatalytic defluorocarboxylation followed by photoinduced iron-catalyzed decarboxylation/isomerization. The reaction involves generating difluoroallyl radicals, tautomerizing to proceeding through radical addition alkylation.

Language: Английский

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Photoinduced Dehalocyclization to Access Oxindoles Using Formate as a Reductant

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(11), P. 1203 - 1208

Published: Feb. 6, 2024

Comprehensive Summary Herein, we report an efficient and practical protocol for the photoinduced dehalocyclization of ortho ‐halophenylacrylamides with formate by engagement a CO 2 radical anion to access substituted oxindoles. This method proceeds smoothly under mild conditions exhibits wide range substrate as well remarkable functional group compatibility.

Language: Английский

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Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8342 - 8356

Published: May 31, 2024

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features this protocol are easy-to-obtain starting materials, a wide range substrates, functional group tolerance as well high atom economy, thus offering strategy to access variety

Language: Английский

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Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF₃ tertiary alcohols

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(15), P. 8694 - 8700

Published: Jan. 1, 2024

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes under an air atmosphere was developed to construct densely functionalized α-CF 3 tertiary alcohols.

Language: Английский

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