Photoredox ketone catalysis for the direct C-H imidation and acyloxylation of arenes

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 m...

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Published inChemical science (Cambridge) Vol. 8; no. 8; pp. 5622 - 5627
Main Authors Tripathi, Chandra Bhushan, Ohtani, Tsuyoshi, Corbett, Michael T., Ooi, Takashi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.08.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
AMINATION
HETEROARENES
ENERGY
ELECTRON-TRANSFER
THIOXANTHONE
QUANTUM YIELDS
TERTIARY-AMINES
LIGHT
EFFICIENT
2+2 PHOTOCYCLOADDITION REACTIONS
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc01700f