4.7 Review

Trivalent Phosphine-Catalyzed Reactions Using Fluorinated Building Blocks

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 365, Issue 15, Pages 2487-2510

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202300381

Keywords

Trivalent phosphine; Fluorination; Addition reaction; Annulation reaction; Organofluorine compound

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This review summarizes the recent advancements in nucleophilic phosphine catalysis for incorporating fluorine/s or fluoroalkyl group/s into organic molecules, focusing on the methodological progress of cycloaddition, addition, and coupling reactions using fluorinated building blocks as electrophilic and/or nucleophilic partners. The article highlights the synthetic strategies, proposed reaction mechanisms, and synthetic utilities of these organofluorine compounds.
The development of novel synthetic methodologies to incorporate fluorine/s or fluoroalkyl group/s into the frameworks of organic molecules has become a highly prioritized research area because such modifications can tune their physiochemical and biological properties. In recent years, nucleophilic phosphine catalysis has been extensively explored to achieve this goal, and significant progress has been made. This review summarizes the methodological advancements of cycloaddition, addition and coupling reactions employing fluorinated building blocks as electrophilic and/or nucleophilic reaction partners under phosphine catalysis to construct structurally and synthetically valuable organofluorine compounds, with special emphasis on the synthetic strategies, proposed reaction mechanisms and synthetic utilities.

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