Observations on transition metal free biaryl coupling: potassium tert-butoxide alone promotes the reaction without diamine or phenanthroline catalysts

Chem Commun (Camb). 2014 Mar 11;50(20):2575-8. doi: 10.1039/c3cc49019j.

Abstract

Biaryl coupling (often labelled 'C-H activation') of aromatic systems can be achieved by potassium tert-butoxide alone in the absence of any amine or bipyridine catalyst (1,10-phenanthroline or N,N'-dimethylethylenediamine being the most common), previously reported to be essential. Various mechanistic studies and observations are presented which suggest that when 1,10-phenanthroline is employed as the catalyst, the alkoxide is destroyed almost immediately.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butanols / chemistry*
  • Catalysis
  • Diamines / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phenanthrolines / chemistry*
  • Transition Elements / chemistry

Substances

  • Butanols
  • Diamines
  • Phenanthrolines
  • Transition Elements
  • tert-butoxide, potassium
  • 1,10-phenanthroline