Regio- and chemoselective metalation of arenes and heteroarenes using hindered metal amide bases

Angew Chem Int Ed Engl. 2011 Oct 10;50(42):9794-824. doi: 10.1002/anie.201101960. Epub 2011 Sep 27.

Abstract

The preparation of highly functionalized organometallic compounds can be achieved by direct C-H activation of a broad range of unsaturated substrates using lithium chloride solubilized 2,2,6,6-tetramethylpiperidide bases (TMP(n)MX(m)⋅p LiCl). These are excellent reagents for converting a wide range of aromatic and heterocyclic substrates into valuable organometallic reagents with broad applications in organic synthesis.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Amides / chemistry*
  • Lithium Chloride / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Piperidines / chemistry*
  • Stereoisomerism

Substances

  • Amides
  • Organometallic Compounds
  • Piperidines
  • 2,2,6,6-tetramethylpiperidide
  • Lithium Chloride