C–F Bond Functionalization: Controlled Didefluorination of <i>o</i>-Trifluoromethyl Benzylamines

Organofluorine compounds are widely used but pose environmental concerns. We report a base-mediated didefluorination of <i>o</i>-trifluoromethyl benzylamines via difluoroquinone methide intermediates, yielding monofluorinated tricyclic 2<i>H</i>-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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Publication Details

Journal
Organic Letters
Published
2025-08-11
DOI
https://doi.org/10.1021/acs.orglett.5c02828
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

C–F Bond Functionalization: Controlled Didefluorination of o-Trifluoromethyl Benzylamines

Seema Dhiman, Mahesh Kumar Ravva, Mahipal Yadav, Rushikesh R. Kusmude et al.
Organic Letters
Fluorine in Organic Chemistry
article

C–F Bond Functionalization: Controlled Didefluorination of o-Trifluoromethyl Benzylamines

Seema Dhiman, Mahesh Kumar Ravva, Mahipal Yadav, Rushikesh R. Kusmude, Siddhant A. Kale
article en

Abstract

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

Organic LettersVol. 27(33)
University of Delhi (IN), SRM University (IN)
SRM Institute of Science and Technology
Life in Land
Openalex Percentile: Top 85%
Fluorine in Organic Chemistry
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