Pd-catalyzed ortho-C-H acylation/cross coupling of aryl ketone O-methyl oximes with aldehydes using tert-butyl hydroperoxide as oxidant

Org Lett. 2010 Sep 3;12(17):3926-9. doi: 10.1021/ol101618u.

Abstract

A Pd-catalyzed protocol for direct C-H bond acylation by cross coupling of aryl ketone oximes and aldehydes using tert-butyl hydroperoxide (TBHP) as oxidant was developed. With oximes as a directing group for the C-H activation, the coupling with aldehydes was achieved with remarkable regioselectivity. The acylation reactions exhibit excellent functional group tolerance, and both aliphatic and heteroaromatic aldehydes can be effectively coupled to the oximes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Aldehydes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Oxidants / chemistry*
  • Oximes / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism
  • tert-Butylhydroperoxide / chemistry*

Substances

  • Aldehydes
  • Ketones
  • Oxidants
  • Oximes
  • Palladium
  • tert-Butylhydroperoxide