Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cationsElectronic supplementary information (ESI) available: NMR spectra and computational data. See DOI: 10.1039/c5sc01973g

Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cationsElectronic supplementary information (ESI) available: NMR spectra and computational data. See DOI: 10.1039/c5sc01973g

Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C-C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ω-fl...

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Bibliographic Details
Main Authors: Pitts, Cody Ross, Bloom, Michelle Sheanne, Bume, Desta Doro, Zhang, Qinze Arthur, Lectka, Thomas
Format: Journal Article
Language:English
Published: 10-08-2015
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Summary:Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C-C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ω-fluoro carboxylic acids, esters, alcohols, and ketones with relative ease. Initial mechanistic insight suggests radical ion intermediates. Unstrained C-C activation via putative radical cation formation promotes a directed radical fluorination event using Selectfluor, catalytic 9-fluorenone, and light.
Bibliography:Electronic supplementary information (ESI) available: NMR spectra and computational data. See DOI
10.1039/c5sc01973g
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc01973g