Preparation of polyfunctional arylzinc organometallics in toluene by halogen/zinc exchange reactions

Moritz Balkenhohl, Dorothée S. Ziegler, Alexandre Desaintjean, Leonie J. Bole, Alan R. Kennedy, Eva Hevia, Paul Knochel

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Abstract

A wide range of polyfunctional diaryl-and diheteroarylzinc species were prepared in toluene within 10 min to 5 h through an I/Zn or Br/Zn exchange reaction using bimetallic reagents of the general formula R’2Zn·2LiOR (R’=sBu, tBu, pTol). Highly sensitive functional groups, such as a triazine, a ketone, an aldehyde, or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of a plethora of functionalized (hetero)arenes after quenching with various electrophiles. Insight into the constitution and reactivity of these bimetallic mixtures revealed the formation of highly active lithium diorganodialkoxyzincates of type[R’2Zn-(OR)2Li2].
Original languageEnglish
Pages (from-to)12898-12902
Number of pages5
JournalAngewandte Chemie International Edition
Volume58
Issue number37
Early online date27 Jun 2019
DOIs
Publication statusPublished - 9 Sep 2019

Keywords

  • alkoxides
  • lithium
  • metal/halogen exchange
  • organozinc reagents
  • toluene

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