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Synthesis 2025; 57(17): 2633-2649
DOI: 10.1055/a-2511-4274
DOI: 10.1055/a-2511-4274
paper
Boryl Radical Chemistry
Synthesis of Trifluoromethyl-Substituted Cyclopentanes through Boron-Radical-Catalyzed Cycloaddition Reaction of Trifluoromethyl-Substituted Alkenes
Authors
Financial support was provided by the National Natural Science Foundation of China (No. 22301237), the Natural Science Basic Research Program of Shaanxi Province (No. 2020JC-08), and the Fundamental Research Funds for the Central Universities (Nos. xtr072022003, xzy012022118).
Abstract
A highly efficient protocol for the synthesis of trifluoromethyl-substituted cyclopentanes, a structural motif ubiquitous in bioactive compounds and natural products, via boron-radical-catalyzed (3+2) cycloaddition of aroylcyclopropanes and trifluoromethyl-substituted alkenes was developed. Employing readily available precursors, this modular, atom-economical, metal-free, and operationally simple process was compatible with diverse functional groups, giving the products in generally good to high yields. Trifluoromethyl-substituted bicyclo[2.1.1]hexanes (BCHs) were analogously prepared.
Key words
cycloaddition - trifluoromethyl-substituted alkenes - boron radicals - catalysis - cyclopentanesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2511-4274.
- Supporting Information (PDF)
- CIF File (ZIP)
Publication History
Received: 29 November 2024
Accepted after revision: 07 January 2025
Accepted Manuscript online:
07 January 2025
Article published online:
14 February 2025
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