Preparation of substituted phenanthridines from the coupling of aryldiazonium salts with nitriles: a metal free approach

J Org Chem. 2015 May 15;80(10):5329-36. doi: 10.1021/acs.joc.5b00579. Epub 2015 May 7.

Abstract

A transition metal free approach for the synthesis of substituted phenanthridines from the coupling reaction of aryldiazonium tetrafluoroborates with nitriles has been developed. This operationally simple protocol proceeds through a substitution of aryldiazonium with nitriles followed by an intramolecular arylation to provide the corresponding phenanthridines in moderate to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Borates
  • Boric Acids / chemistry*
  • Catalysis
  • Diazonium Compounds / chemistry*
  • Metals / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / chemistry
  • Salts / chemistry*

Substances

  • Borates
  • Boric Acids
  • Diazonium Compounds
  • Metals
  • Nitriles
  • Phenanthridines
  • Salts
  • benzenediazonium
  • fluoroboric acid