Preparation of unsymmetrical ketones from tosylhydrazones and aromatic aldehydes via formyl C-H bond insertion

Org Lett. 2014 Jun 6;16(11):3064-7. doi: 10.1021/ol5011714. Epub 2014 May 12.

Abstract

Preparation of ketones by insertion of diazo compounds into the formyl C-H bond of an aldehyde is an attractive procedure, but use of structurally diverse diazo compounds is hampered by preparation and safety issues. A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable tosylhydrazones and aryl aldehydes is reported. The procedure can be performed in one pot from the parent carbonyl compound and needs only a base, with no additional promoters being required.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Azo Compounds / chemistry*
  • Catalysis
  • Hydrazones / chemistry*
  • Hydrogen Bonding
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure

Substances

  • Aldehydes
  • Azo Compounds
  • Hydrazones
  • Ketones