Work

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

Year: 2013

Type: article

Abstract: 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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja410478a

Authors: Filip R. Petronijević, Manuel Nappi, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funder: National Institute of General Medical Sciences

Award: Combining Nickel and Photoredox Catalysis