Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes

J Org Chem. 2011 Mar 18;76(6):1707-14. doi: 10.1021/jo102366q. Epub 2011 Feb 22.

Abstract

Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl(3) (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chlorobenzenes / chemistry
  • Indicators and Reagents / chemistry
  • Indium / chemistry
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Substrate Specificity
  • Tin Compounds / chemistry*

Substances

  • Chlorobenzenes
  • Indicators and Reagents
  • Ketones
  • Tin Compounds
  • Indium
  • stannane
  • chlorobenzene