Issue 9, 2015
From the journal:

Chemical Science

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

Cody Ross Pitts,a   Michelle Sheanne Bloom,a   Desta Doro Bume,a   Qinze Arthur Zhanga  and  Thomas Lectka*a  

* Corresponding authors

a Department of Chemistry, Johns Hopkins University, Baltimore, MD, USA
E-mail: Lectka@jhu.edu

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

DOI
https://doi.org/10.1039/C5SC01973G
Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2015,6, 5225-5229

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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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