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Ketones as directing groups in photocatalytic sp3 C–H fluorination

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Abstract

The ubiquitous ketone carbonyl group generally deactivates substrates toward radical-based fluorinations, especially sites closest to it. Herein, ketones are used instead to direct aliphatic fluorination using Selectfluor, catalytic benzil, and visible light. Selective β- and γ-fluorination are demonstrated on rigid mono-, di-, tri-, and tetracyclic (steroidal) substrates employing both cyclic and exocyclic aliphatic ketones as directing groups.

Graphical abstract: Ketones as directing groups in photocatalytic sp3 C–H fluorination

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Publication details

The article was received on 16 Jun 2017, accepted on 10 Aug 2017 and first published on 11 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02703F
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Ketones as directing groups in photocatalytic sp3 C–H fluorination

    D. D. Bume, C. R. Pitts, F. Ghorbani, S. A. Harry, J. N. Capilato, M. A. Siegler and T. Lectka, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC02703F

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