TY - JOUR
T1 - Direct β-functionalization of cyclic ketones with aryl ketones via the merger of photoredox and organocatalysis
AU - Petronijević, Filip R.
AU - Nappi, Manuel
AU - MacMillan, David W.C.
PY - 2013/12/11
Y1 - 2013/12/11
N2 - 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.
AB - 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.
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U2 - 10.1021/ja410478a
DO - 10.1021/ja410478a
M3 - Article
C2 - 24237366
AN - SCOPUS:84890447091
SN - 0002-7863
VL - 135
SP - 18323
EP - 18326
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 49
ER -