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DOI: 10.1055/s-0029-1217944
Photoredox Organocatalysis: Asymmetric α-Perfluoroalkylation of Aldehydes
D. A. Nagib, M. E. Scott, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, USA
Publikationsverlauf
Publikationsdatum:
22. September 2009 (online)

Significance
MacMillan and co-workers report an efficient and highly enantioselective α-perfluoroalkylation of aldehydes employing photoredox organocatalysis. The proposed mechanism involves an organocatalytic and a photoredox catalytic cycle. The organocatalyst 1 reacts with the aldehyde to form an enamine intermediate which reacts with the trifluoromethyl radical, formed in the photoredox catalytic cycle. The resulting α-amino radical is oxidized by an excited state species of the photocatalyst 2, generated by irradiation. The reduced photocatalyst is reoxidized by trifluoromethyliodide to give 2 and a new trifluoromethyl radical.