1,1‐Disubstituted Vinylbromides: Versatile Building Blocks for the Synthesis of Nitrogen‐Containing Heterocycles

1,1‐Disubstituted vinyl bromides have emerged as powerful and versatile building blocks for the synthesis of nitrogen‐containing heterocycles. Their dual functionality—encompassing both a reactive bromide and a polarized CC bond—enables diverse transformations including cycloadditions, metal‐catalyzed couplings, lithiation, and radical or cascade processes. This review summarizes recent advances up to 2025 in the preparation of aziridines, pyrroles, indoles, indolizines, pyrrolidines, pyrazoles, triazoles, isoxazoles, isoxazolidines, and piperidines derived from these substrates. Particular attention is given to regio‐ and stereoselective strategies, the construction of fluorinated and functionalized heterocycles, and applications in medicinal chemistry.

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Journal
European Journal of Organic Chemistry
Published
2026-04-27
DOI
https://doi.org/10.1002/ejoc.202501199
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

1,1‐Disubstituted Vinylbromides: Versatile Building Blocks for the Synthesis of Nitrogen‐Containing Heterocycles

Jun Fang, Gérard Guillamot, Anne Westermeyer, Guillaume Lefèvre et al.
European Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

1,1‐Disubstituted Vinylbromides: Versatile Building Blocks for the Synthesis of Nitrogen‐Containing Heterocycles

Jun Fang, Gérard Guillamot, Anne Westermeyer, Guillaume Lefèvre, C. Tony Liu, Phannarath Phansavath, Virginie Ratovelomanana‐Vidal
article en

Abstract

1,1‐Disubstituted vinyl bromides have emerged as powerful and versatile building blocks for the synthesis of nitrogen‐containing heterocycles. Their dual functionality—encompassing both a reactive bromide and a polarized CC bond—enables diverse transformations including cycloadditions, metal‐catalyzed couplings, lithiation, and radical or cascade processes. This review summarizes recent advances up to 2025 in the preparation of aziridines, pyrroles, indoles, indolizines, pyrrolidines, pyrazoles, triazoles, isoxazoles, isoxazolidines, and piperidines derived from these substrates. Particular attention is given to regio‐ and stereoselective strategies, the construction of fluorinated and functionalized heterocycles, and applications in medicinal chemistry.

European Journal of Organic Chemistry
Centre National de la Recherche Scientifique (FR), ParisTech (FR), Université Paris Sciences et Lettres (FR), Groupe SEB (FR), Institut de Recherche de Chimie Paris (FR)
Openalex Percentile: Top 8%
Catalytic C–H Functionalization Methods
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1,1‐Disubstituted Vinylbromides: Versatile Building Blocks for the Synthesis of Nitrogen‐Containing Heterocycles — Jun Fang, Gérard Guillamot, et al. · European Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS