The divergent synthesis of nitrogen heterocycles by rhodium(II)-catalyzed cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes

Angew Chem Int Ed Engl. 2014 May 26;53(22):5662-6. doi: 10.1002/anie.201400426. Epub 2014 Apr 11.

Abstract

The first rhodium(II)-catalyzed aza-[4+3] cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes have been developed, and enable the efficient synthesis of highly functionalized 2,5-dihydroazepines from readily available precursors. In some cases, the reaction pathway could divert to formal aza-[3+2] cycloadditions, thus leading to 2,3-dihydropyrroles. In this context, the titled reaction represents a capable tool for the divergent synthesis of two types of synthetically valuable aza-heterocycles from common rhodium(II) iminocarbene intermediates.

Keywords: carbenes; cycloaddition; nitrogen heterocycles; rhodium; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry*
  • Azepines / chemistry
  • Catalysis
  • Cycloaddition Reaction
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Nitrogen / chemistry
  • Rhodium / chemistry*
  • Triazoles / chemistry*

Substances

  • Alkadienes
  • Azepines
  • Heterocyclic Compounds
  • Triazoles
  • carbene
  • Rhodium
  • Nitrogen
  • Methane