Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
The syntheses of substituted all-cis-1,2,3-trifluorocyclopropanes are described for the first time. The three fluorines located on each of the cyclopropyl carbons with a stereochemistry where they are all on the same face of the cyclopropane, imparts a significant polarity to the molecule, and the inherent conformational rigidity and lowering of log P makes this motif attractive for exploration as a substituent for pharmaceuticals and agrochemicals research.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c9cc05749h | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Thermodynamics and polarity-driven properties of fluorinated cyclopropanes.
Beilstein J Org Chem
August 2025
Department of Chemistry, Institute of Natural Sciences, Federal University of Lavras, 37200-900, Lavras, MG, Brazil.
Cyclopropane is a significant alicyclic motif, widely utilized in medicinal chemistry, while fluorination serves as a powerful tool to modulate properties that enhance the performance of pharmaceuticals and materials. This quantum-chemical study explores the energetic implications of fluorinating cyclopropane, providing insights into molecular characteristics arising from the polar C-F bond. Isodesmic reactions revealed that the conversion of cyclopropane and methyl fluoride into mono-, di-, tri-, tetra-, penta-, and hexafluorinated cyclopropanes is exothermic, except for the all--1,2,3-trifluorocyclopropane ().
View Article and Find Full Text PDFAccess to -Diindolylcyclopropanes via Double Indolylation of -Difluorocyclopropanes.
J Org Chem
August 2025
School of Chemistry and Chemical Engineering, Linyi University, Linyi 276000, China.
gem-Difluorocyclopropanes (-DFCPs) have gained significant attention as versatile fluorinated synthons in organic synthesis due to their unique structural and electronic properties. Recent advancements have demonstrated the utility of -DFCPs in transition-metal-catalyzed cross-coupling reactions with indoles, enabling the synthesis of monofluoroallylic indole derivatives. In this study, a transition-metal-free double indolylation of -DFCPs was developed, preserving the cyclopropane core and facilitating the direct incorporation of two indole units.
View Article and Find Full Text PDF[1,3]-Hydride Shift in α-Boryl Cations: Strategic Design of Fluorine-Triggered Cyclopropanation.
J Am Chem Soc
July 2025
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang 37673, Republic of Korea.
Hydride shift represents an important process in carbocation chemistry, yet controlled access to the [1,3]-hydride shift has remained elusive despite its potential synthetic utility. Here, we report direct observation and synthetic demonstration of the [1,3]-hydride shift using α-fluoro-diborylalkanes. Initial [1,2]-fluoride migration generates an α-boryl cation that selectively undergoes a [1,3]-hydride shift via a three-center two-electron interaction, enabling efficient synthesis of cyclopropyl boronic esters.
View Article and Find Full Text PDFElementary Steps in Olefin Metathesis: Nickelacyclobutanes via Cycloaddition to Nickel Carbenes.
J Am Chem Soc
July 2025
Centre for Catalysis Research & Innovation and Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, ON K1N 6N5, Canada.
Olefin metathesis and cyclopropanation, major reactions in the synthetic toolbox, are predominantly catalyzed by platinum-group metals. First-row transition metal alternatives are desirable from the perspective of supply-chain sustainability. Although cyclopropanation by nickel catalysts is well established, limited evidence exists for the chemical feasibility of the cycloaddition step essential for inner-sphere cyclopropanation or olefin metathesis.
View Article and Find Full Text PDFFluorinated cyclopropanes for 2-heterosubstituted electron-rich indolizine synthesis.
Org Biomol Chem
July 2025
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia.
Fluorinated cyclopropanes were proven to be valuable precursors for a wide range of 2-heterosubstituted electron-rich indolizines, hardly accessible by other methods due to their instability. Copper(I) activation of C-X bonds permits disubstituted fluorocyclopropanes to undergo ring opening in the presence of pyridines, yielding (2-fluoroallyl)pyridinium salts. These intermediates were found to undergo base-promoted cyclization, either retaining the fluorine atom or undergoing intermolecular fluorine substitution with additional , producing two- or three-component-derived 2-,,,-subtituted indolizines.
View Article and Find Full Text PDF