Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates
Maxim Ratushnyy
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
Search for more papers by this authorNikita Kvasovs
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.
Search for more papers by this authorSumon Sarkar
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.
Search for more papers by this authorCorresponding Author
Prof. Vladimir Gevorgyan
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
Search for more papers by this authorMaxim Ratushnyy
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
Search for more papers by this authorNikita Kvasovs
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.
Search for more papers by this authorSumon Sarkar
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.
Search for more papers by this authorCorresponding Author
Prof. Vladimir Gevorgyan
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
Search for more papers by this authorAbstract
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.
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