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. 2015 Sep 1;6(9):5225-5229.
doi: 10.1039/c5sc01973g. Epub 2015 Jun 23.

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

Cody Ross Pitts  1 , Michelle Sheanne Bloom  1 , Desta Doro Bume  1 , Qinze Arthur Zhang  1 , Thomas Lectka  1
Affiliations

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

Cody Ross Pitts et al. Chem Sci. .

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.

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Figures

Scheme 1
Scheme 1. Concept for selective C–C fragmentation/C–F formation.
Scheme 2
Scheme 2. Control reaction.
Scheme 3
Scheme 3. Standard reaction conditions.
Scheme 4
Scheme 4. Intermolecular competition experiments.
Scheme 5
Scheme 5. Isodesmic analysis at B3PW91/6-311++G**(MeCN).
See this image and copyright information in PMC

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