Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol

Org Lett. 2007 Apr 12;9(8):1521-4. doi: 10.1021/ol0702829. Epub 2007 Mar 16.

Abstract

[reaction: see text] An SN2 mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxylamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Bromides / chemistry
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Electrons*
  • Molecular Structure
  • Piperidines / chemistry
  • Zinc / chemistry*

Substances

  • Bromides
  • Piperidines
  • piperidine
  • Copper
  • Zinc