Room-temperature photoinduced direct C-H-arylation via base-promoted homolytic aromatic substitution

Org Lett. 2013 Mar 15;15(6):1174-7. doi: 10.1021/ol3034687. Epub 2013 Mar 6.

Abstract

Conceptually different approach toward biaryl syntheses by photoinduced direct C-H arylation of benzene and thiophene in the presence of t-BuOK is reported. The reaction proceeds through photo- and base-promoted homolytic aromatic substitution. The o-, m- and p- substituted ArI, as well as the electron-donating and electron-withdrawing nature of the substituents were found be good to excellent substrates. Heteroaryl, ArBr, ArCl and double C-H arylation were successfully achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Photochemical Processes
  • Temperature
  • Thiophenes / chemistry*

Substances

  • Benzene Derivatives
  • Thiophenes