One-step synthesis of 3-aryl- and 3,4-diaryl-(1H)-pyrroles using tosylmethyl isocyanide (TOSMIC)

Org Lett. 2002 Oct 3;4(20):3537-9. doi: 10.1021/ol0267073.

Abstract

A one-step synthesis of 3-aryl and 3,4-diaryl-(1H)-pyrroles from TOSMIC and commercially available or readily synthesized arylalkenes is reported. Optimal conditions were found to be NaOtBu in DMSO. The methodology was particularly efficient (yields > 65%) when electron poor aryl groups were attached to the alkene.[ reaction: see text]

MeSH terms

  • Cyanides / chemistry*
  • Molecular Structure
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*

Substances

  • Cyanides
  • Porphyrins
  • Pyrroles
  • tosylmethyl isocyanide