Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
A Ru-catalyzed defluorinative cyclization of polyfluoroalkyl tetralones has been developed under visible-light irradiation for the precise assembly of γ-pyrones featuring α-perfluoroalkyl and β-fluorine substituents. Selective functionalization of five C(sp)-F bonds at three carbon sites on the perfluoroalkyl chain provides a new mode for utilizing polyfluorides as versatile synthons to access difficult-to-obtain heterocyclic scaffolds. Moreover, the sulfinate salt serves dual roles as an oxygen source for creating the carbonyl group and as a defluorinating promoter.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.5c00214 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Controllable Defluorinative Cyclization for Divergent Synthesis of Pyrrolo[2,3-]pyrimidines and Fluorinated Pyrimidines from β-CF-1,3-Enynes and Amidine Hydrochlorides.
Org Lett
July 2025
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
This study successfully developed a novel controllable defluorinative cyclization strategy for β-CF-1,3-enynes, achieving the divergent synthesis of pyrrolo[2,3-]pyrimidines and fluorinated pyrimidines. The reaction between β-CF-1,3-enynes and amidine hydrochlorides at a 1:2 molar ratio triggered selective [3+3]/[4+1] defluorinative cyclization, which efficiently constructed the pyrrolo[2,3-]pyrimidine framework. Notably, this work first reported that the process achieved cleavage/annulation of triple C-F bonds in the CF group of β-CF-1,3-enynes in a single step.
View Article and Find Full Text PDFPhotocatalytic Reactions of α-CF Alkenes with Alcohols by Controllable Non-, Mono- and Dual-Defluorination.
Org Lett
July 2025
Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control, School of Light Industrial and Food Engineering, Guangxi University, Nanning 530004, China.
Herein, we present a chemoselective strategy for the divergent synthesis of γ-trifluoromethyl alcohols and difluorohomoallyl alcohols via photoredox-catalyzed hydroxyalkylation of α-CF alkenes with primary/secondary alcohols. Both products can further undergo base-mediated intramolecular defluorinative cyclization to construct monofluorinated dihydrofurans in a one-pot process. Through controllable C-F bond cleavage, this approach enables streamlined synthesis of three types of fluorinated products from abundant and inexpensive raw materials under mild photoredox conditions.
View Article and Find Full Text PDFFluoroalkylacylsilanes as Novel Ambiphilic Donor-Acceptor Carbene Precursors.
Acc Chem Res
May 2025
The Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan 430072, China.
ConspectusCarbenes, as highly reactive intermediates, have emerged as pivotal tools in organic synthesis, catalysis, and materials science due to their versatile reactivity and broad applicability. Among the diverse classes of carbenes, donor-acceptor carbenes (DACs) have attracted significant attention owing to their unique electronic properties and exceptional reaction selectivity. The distinctive reactivity of DACs arises from the synergistic electronic interplay between electron-withdrawing and electron-donating groups attached to the carbene center, enabling a wide array of transformations.
View Article and Find Full Text PDFHydrocyclization/Defluorination of CF-Substituted Acrylamides: Insights from Kinetics of Hydrogen Atom Transfer.
Adv Sci (Weinh)
July 2025
Department of Chemistry, Columbia University, 3000 Broadway, New York, NY, 10027, USA.
The introduction of F-containing groups into organic molecules can significantly alter their physical and chemical properties. Particularly, gem-difluoroalkenes serve as versatile precursors for a broad variety of organofluorine compounds, commonly used in agrochemicals, pharmaceuticals, and materials science. Based on the kinetics of H• transfer to acrylamide (k = 2.
View Article and Find Full Text PDFPhotocatalyzed/Base-Mediated Defluorinative Three-Component Cascade Cyclization: Access to Monofluorocyclohexenes and 6-Fluoro-1,2,3,4-tetrahydropyridines.
Org Lett
March 2025
Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control, School of Light Industrial and Food Engineering, Guangxi University, Nanning 530004, China.
A three-component cascade cyclization of α-CF alkenes, electron-rich alkenes, and dimethyl esters or sulfonamides via a dual C-F bond cleavage process is described. This methodology provides a general and efficient strategy to access monofluorocyclohexenes and 6-fluoro-1,2,3,4-tetrahydropyridines by switching the bifunctional reagents (dimethyl esters or sulfonamides), which are valuable building blocks in synthetic chemistry and the pharmaceutical industries. The reaction mechanism and the synthetic applications of the products have been demonstrated.
View Article and Find Full Text PDF