Rapid and efficient microwave-assisted copper(0)-catalyzed ullmann coupling reaction: general access to anilinoanthraquinone derivatives

Org Lett. 2007 Mar 29;9(7):1271-4. doi: 10.1021/ol070102v. Epub 2007 Mar 10.

Abstract

[structure: see text]. The synthesis of anilinoanthraquinones 3a-z was achieved by a new, Cu(0)-catalyzed, microwave-assisted Ullmann coupling reaction of bromaminic acid (1) with aniline derivatives 2a-z in phosphate buffer. Good to excellent isolated yields were obtained within only 2-20 min at 80-120 degrees C and 40-100 W. The new procedure provides the first general access to anilinoanthraquinones, furnishing a number of previously inaccessible compounds. It is superior to classical methods in all aspects, including yields, reaction time, and versatility.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds* / chemical synthesis
  • Aniline Compounds* / chemistry
  • Anthraquinones* / chemical synthesis
  • Anthraquinones* / chemistry
  • Buffers
  • Catalysis
  • Copper / chemistry*
  • Microwaves*
  • Molecular Structure
  • Time Factors

Substances

  • Aniline Compounds
  • Anthraquinones
  • Buffers
  • Copper
  • bromamine acid