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Pitts CR, Bloom MS, Bume DD, et al. Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations. Chem Sci. 2015;6(9):5225-5229doi: 10.1039/c5sc01973g.
Pitts, C. R., Bloom, M. S., Bume, D. D., Zhang, Q. A., & Lectka, T. (2015). Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations. Chemical science, 6(9), 5225-5229. https://doi.org/10.1039/c5sc01973g
Pitts, Cody Ross, et al. "Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations." Chemical science vol. 6,9 (2015): 5225-5229. doi: https://doi.org/10.1039/c5sc01973g
Pitts CR, Bloom MS, Bume DD, Zhang QA, Lectka T. Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations. Chem Sci. 2015 Sep 01;6(9):5225-5229. doi: 10.1039/c5sc01973g. Epub 2015 Jun 23. PMID: 29449927; PMCID: PMC5669245.
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Chem Sci. 2015 Sep 01;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.

Chemical science

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

Affiliations

  1. Department of Chemistry , Johns Hopkins University , Baltimore , MD , USA . Email: [email protected].

PMID: 29449927 PMCID: PMC5669245 DOI: 10.1039/c5sc01973g

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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