A mild, ferrocene-catalyzed C-H imidation of (hetero)arenes

J Am Chem Soc. 2014 Apr 9;136(14):5279-82. doi: 10.1021/ja501879c. Epub 2014 Mar 31.

Abstract

A simple method for direct C-H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reaction is broad, the conditions are extremely mild, and the reaction is tolerant of oxidizable and acid-labile functionality, multiple heteroatoms, and aryl iodides. Mechanistic studies indicate that ferrocene (Cp2Fe) plays the role of an electron shuttle in the decomposition of the perester reagent, delivering a succinimidyl radical ready to add to an aromatic system.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry*
  • Catalysis
  • Ferrous Compounds / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Imides / chemical synthesis*
  • Imides / chemistry
  • Metallocenes
  • Molecular Structure

Substances

  • Benzene Derivatives
  • Ferrous Compounds
  • Heterocyclic Compounds
  • Imides
  • Metallocenes
  • ferrocene