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Direct β‑Functionalization of Cyclic Ketones with Aryl Ketones via the Merger of Photoredox and Organocatalysis

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posted on 2013-12-11, 00:00 authored by Filip R. Petronijević, Manuel Nappi, David W. C. MacMillan
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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