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Issue 8, 2017
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Photoredox ketone catalysis for the direct C–H imidation and acyloxylation of arenes

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Abstract

The photoexcited aryl ketone-catalyzed C–H imidation of arenes and heteroarenes is reported. Using 3,6-dimethoxy-9H-thioxanthen-9-one as a catalyst in combination with a bench-stable imidating reagent, C–N bond formation proceeds with high efficiency and a broad substrate scope. A key part of this method is that the thioxanthone catalyst acts as an excited-state reductant, thus establishing an oxidative quenching cycle for radical aromatic substitution. The synthetic potential of this photoexcited ketone catalysis is further demonstrated by application to the direct C–H acyloxylation of arenes.

Graphical abstract: Photoredox ketone catalysis for the direct C–H imidation and acyloxylation of arenes

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Publication details

The article was received on 17 Apr 2017, accepted on 04 Jun 2017 and first published on 05 Jun 2017


Article type: Edge Article
DOI: 10.1039/C7SC01700F
Citation: Chem. Sci., 2017,8, 5622-5627
  • Open access: Creative Commons BY license
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    Photoredox ketone catalysis for the direct C–H imidation and acyloxylation of arenes

    C. B. Tripathi, T. Ohtani, M. T. Corbett and T. Ooi, Chem. Sci., 2017, 8, 5622
    DOI: 10.1039/C7SC01700F

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