Copper-catalyzed one-pot synthesis of unsymmetrical arylurea derivatives via tandem reaction of diaryliodonium salts with N-arylcyanamide

J Org Chem. 2014 Sep 5;79(17):8156-62. doi: 10.1021/jo501334u. Epub 2014 Aug 18.

Abstract

An efficient "one-pot" approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Cyanamide / chemistry*
  • Onium Compounds / chemistry*
  • Stereoisomerism
  • Urea / analogs & derivatives
  • Urea / chemical synthesis*
  • Urea / chemistry*

Substances

  • Onium Compounds
  • Cyanamide
  • Copper
  • Urea