Overcoming Back Electron Transfer in the Electron Donor-Acceptor Complex-Mediated Visible Light-Driven Generation of α-Aminoalkyl Radicals from Secondary Anilines

J Org Chem. 2023 Jan 6;88(1):462-474. doi: 10.1021/acs.joc.2c02448. Epub 2022 Dec 8.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Amino Acids / chemistry
  • Aniline Compounds*
  • Electrons*
  • Light
  • Oxidants

Substances

  • Aniline Compounds
  • Amines
  • Oxidants
  • Amino Acids