Phenyl hydrazine as initiator for direct arene C-H arylation via base promoted homolytic aromatic substitution

Org Lett. 2013 Dec 6;15(23):6102-5. doi: 10.1021/ol402995e. Epub 2013 Nov 19.

Abstract

A simple and efficient direct radical arylation of unactivated arenes is described which uses cheap and commercially available phenyl hydrazine as an initiator. The reaction occurs through a base promoted homolytic aromatic substitution (BHAS) mechanism involving aryl radicals and aryl radical anions as intermediates and offers a practical approach for preparation of an array of substituted biaryls.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Benzene Derivatives / chemistry*
  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / chemistry
  • Catalysis
  • Molecular Structure
  • Phenylhydrazines / chemistry*

Substances

  • Benzene Derivatives
  • Biphenyl Compounds
  • Phenylhydrazines
  • phenylhydrazine