Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 49, Pages 18323-18326Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja410478a
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- NIGMS [R01 GM103558-01]
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The direct beta-coupling of cyclic ketones with aryl ketones has been achieved via the synergistic combination of photoredox catalysis and organocatalysis. Diaryl oxymethyl or aryl-alkyl oxymethyl radicals, transiently generated via single-electron reduction of ketone precursors, readily merge with beta-enaminyl radical species, generated by photon-induced enamine oxidation, to produce gamma-hydroxyketone adducts. Experimental evidence indicates that two discrete reaction pathways can be operable in this process depending upon the nature of the ketyl radical precursor and the photocatalyst.
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