High Yielding Lithiation of Azobenzenes by Tin-Lithium Exchange

Jan Strueben, Matthias Lipfert, Jan-Ole Springer, Colin A Gould, Paul J Gates, Frank Sönnichsen, Anne Staubitz

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The lithiation of halogenated azobenzenes by a halogen-lithium exchange commonly leads to a substantial degradation of the azo-group to give hydrazine derivatives besides the desired aryl-lithium species. Yields for quenching reactions with electrophiles are therefore low. This work shows that a transmetalation reaction of easily accessible stannylated azobenzenes with methyl lithium leads to a near-quantitative lithiation of azobenzenes in para, meta and ortho position. To investigate the scope of the reaction, various lithiated azobenzenes species were quenched with a variety of electrophiles. Furthermore, mechanistic 119-Sn NMR spectroscopic studies on the formation of lithiated azobenzenes are presented. A tin-ate complex of the azobenzene could be detected at low temperatures.
Original languageEnglish
Number of pages9
JournalChemistry - A European Journal
Early online date26 Jun 2015
Publication statusPublished - 2015

Bibliographical note

Date of Acceptance: 06/05/2015


  • azo compounds
  • lithiation
  • metalation
  • synthetic methods
  • tin


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