Metal-free, visible-light-mediated direct C-H arylation of heteroarenes with aryl diazonium salts

J Am Chem Soc. 2012 Feb 15;134(6):2958-61. doi: 10.1021/ja212099r. Epub 2012 Feb 3.

Abstract

Visible light along with 1 mol % eosin Y catalyzes the direct C-H bond arylation of heteroarenes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and heteroarenes. The general and easy procedure provides a transition-metal-free alternative for the formation of aryl-heteroaryl bonds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Catalysis
  • Cyclic N-Oxides / chemistry
  • Diazonium Compounds / chemistry*
  • Hydrogen / chemistry
  • Light
  • Magnetic Resonance Spectroscopy / methods
  • Materials Testing
  • Metals / chemistry*
  • Models, Chemical
  • Oxidation-Reduction
  • Palladium / chemistry
  • Photochemistry / methods
  • Pyrroles / chemistry
  • Salts / chemistry*
  • Transition Elements / chemistry

Substances

  • Cyclic N-Oxides
  • Diazonium Compounds
  • Metals
  • Pyrroles
  • Salts
  • Transition Elements
  • Palladium
  • Carbon
  • Hydrogen
  • TEMPO