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Published on: June 21, 2017
Gold-Mediated Cyclization of N-Acrylamides via Energy Transfer Photocatalysis
Yuan Zhao1, Sébastien G Guillet1, Vladislav A Voloshkin1
1Department of Chemistry, Centre for Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000 Ghent, Belgium.
Abstract:
We disclose a gold-mediated photocyclization method for the efficient synthesis of acrylamide-derived β-lactams and 3,4-dihydroquinolin-2-ones, two privileged bioactive scaffolds. The protocol proceeds with ease, providing good yields of product while exhibiting excellent functional group tolerance at low catalyst loadings in sustainable solvents. Additionally, reaction times are significantly reduced compared with prior-art methods. Notably, the present gold system exhibits superior performance in activating poorly conjugated substrates, which are typically unreactive with other photocatalysts, highlighting the exceptional position of this organogold system among modern photocatalysts.
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