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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Overcoming Back Electron Transfer in the Electron Donor-Acceptor Complex-Mediated Visible Light-Driven Generation of
August Runemark1, Henrik Sundén1,2
1Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Kemivägen 10, Gothenburg 412 96, Sweden.
Abstract:
An additive-free, visible light-driven annulation between N-aryl amino acids and maleimide to form tetrahydroquinolines (THQs) is disclosed. Photochemical activation of an electron donor-acceptor (EDA) complex between amino acids and maleimides drives the reaction, and aerobic oxygen acts as the terminal oxidant in the net oxidative process. A range of N-aryl amino acids and maleimides have been investigated as substrates to furnish the target THQ in good to excellent yield. Mechanistic investigations, including titration and UV-vis studies, demonstrate the key role of the EDA complex as the photoactive species.
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