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Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates |
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| Authors: | Maxim Ratushnyy Nikita Kvasovs Sumon Sarkar Prof Vladimir Gevorgyan |
| Institution: | 1. Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL, 60607-7061 USA
Department of Chemistry and Biochemistry, University of Texas at Dallas, 800 West Campbell, BSB13, Richardson, TX, 75080 USA;2. Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL, 60607-7061 USA Department of Chemistry and Biochemistry, University of Texas at Dallas, 800 West Campbell, BSB13, Richardson, TX, 75080 USA These authors contributed equally to this work.;3. Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL, 60607-7061 USA |
| Abstract: | A mild visible-light-induced Pd-catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage of a C(sp2)−O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions. |
| Keywords: | homolysis light-mediated reactions palladium radicals triflates |