Direct β-functionalization of cyclic ketones with aryl ketones via the merger of photoredox and organocatalysis.
The direct β-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 β-enaminyl radical species, generated by photon-induced enamine oxidation, to produce γ-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.
Merck Center for Catalysis at Princeton University , Princeton, New Jersey 08544, United States.
Filip R
FR
Petronijević
Manuel
M
Nappi
David W C
DW
MacMillan
D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D010084:Oxidation-Reduction; D055668:Photochemical Processes
D007659:Ketones; D009930:Organic Chemicals