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

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Balkenhohl, Moritz and Ziegler, Dorothée S. and Desaintjean, Alexandre and Bole, Leonie J. and Kennedy, Alan R. and Hevia, Eva and Knochel, Paul (2019) Preparation of polyfunctional arylzinc organometallics in toluene by halogen/zinc exchange reactions. Angewandte Chemie International Edition, 58 (37). pp. 12898-12902. ISSN 1521-3773 (https://doi.org/10.1002/anie.201906898)

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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].

ORCID iDs

Balkenhohl, Moritz, Ziegler, Dorothée S., Desaintjean, Alexandre, Bole, Leonie J., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506 and Knochel, Paul;
  • Item type:Article
    ID code:71072
    Dates:
    Date
    Event
    9 September 2019
    Published
    27 June 2019
    Published Online
    3 June 2019
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:10 Jan 2020 15:56
    Last modified:12 Dec 2024 09:08
    URI:https://strathprints.strath.ac.uk/id/eprint/71072
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