Practical approach for preparation of unsymmetric benzils from β-ketoaldehydes

Org Lett. 2014 Feb 7;16(3):733-5. doi: 10.1021/ol403762e. Epub 2014 Jan 29.

Abstract

An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones from β-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Decarboxylation
  • Halogenation
  • Ketones / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Phenylglyoxal / analogs & derivatives*
  • Phenylglyoxal / chemical synthesis
  • Phenylglyoxal / chemistry
  • Sodium Hypochlorite / chemistry*

Substances

  • Aldehydes
  • Ketones
  • Sodium Hypochlorite
  • Phenylglyoxal
  • benzil