New preparation of TMPZnCl·LiCl by Zn insertion into TMPCl. Application to the functionalization of dibromodiazines

Org Lett. 2013 Mar 1;15(5):1128-31. doi: 10.1021/ol400248e. Epub 2013 Feb 19.

Abstract

A practical zinc insertion starting from cheap commercial zinc powder and TMPCl (1-chloro-2,2,6,6-tetramethylpiperidine) allows a fast and efficient synthesis of the zinc base TMPZnCl·LiCl under mild conditions in high yields. This base is kinetically highly active and was used for the regio- and chemoselective functionalization of dibromodiazines (pyridazines and pyrazines).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry*
  • Lithium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Piperidines / chemistry*
  • Pyridazines / chemical synthesis*
  • Pyridazines / chemistry
  • Stereoisomerism
  • Zinc / chemistry*

Substances

  • 1-chloro-2,2,6,6-tetramethylpiperidine
  • Hydrocarbons, Chlorinated
  • Organometallic Compounds
  • Piperidines
  • Pyridazines
  • Lithium
  • Zinc