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Issue 9, 2015
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Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations

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Abstract

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.

Graphical abstract: Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations

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Article information


Submitted
02 Jun 2015
Accepted
22 Jun 2015
First published
23 Jun 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 5225-5229
Article type
Edge Article
Author version available

Unstrained C–C bond activation and directed fluorination through photocatalytically-generated radical cations

C. R. Pitts, M. S. Bloom, D. D. Bume, Q. A. Zhang and T. Lectka, Chem. Sci., 2015, 6, 5225
DOI: 10.1039/C5SC01973G

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