C-F Bond Functionalization: Controlled Didefluorination of

Siddhant A Kale; Rushikesh R. Kusmude; Mahesh Kumar Ravva; Mahipal Yadav; Seema Dhiman

doi:10.1021/acs.orglett.5c02828

August 11, 2025

C-F Bond Functionalization: Controlled Didefluorination of

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Key Points

The core contribution reveals a base-mediated didefluorination process for organofluorine compounds.
Base-mediated reactions transform o-trifluoromethyl benzylamines into monofluorinated imidazoles efficiently.
This method provides a broad substrate scope, confirming its applicability in various conditions.
Understanding the mechanistic insight enhances knowledge of fluoride ion elimination pathways in organic chemistry.

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Implication

Base-mediated didefluorination improves organofluorine management, highlighting the mechanistic pathway in tricyclic compounds.

Abstract

Organofluorine compounds are widely used but pose environmental concerns. We report a base-mediated didefluorination of o-trifluoromethyl benzylamines via difluoroquinone methide intermediates, yielding monofluorinated tricyclic 2H-imidazoles. This efficient method showcases a broad substrate scope and offers mechanistic insight through a 1,4-elimination pathway of two fluoride ions.

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Cite This Study

Kale et al. (2025) studied this question.

synapsesocial.com/papers/689e03d9d61984b91e13cc4b https://doi.org/10.1021/acs.orglett.5c02828

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C-F Bond Functionalization: Controlled Didefluorination of

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C-F Bond Functionalization: Controlled Didefluorination of

Key Points

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Abstract

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