N-Acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes

J Am Chem Soc. 2014 Apr 16;136(15):5607-10. doi: 10.1021/ja501906x. Epub 2014 Apr 4.

Abstract

This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amination
  • Hydrocarbons / chemistry*
  • Light*
  • Nitrogen / chemistry*
  • Phthalimides / chemistry*
  • Temperature

Substances

  • Hydrocarbons
  • Phthalimides
  • Nitrogen