Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene

Armstrong, D.R. and Balloch, L. and Clegg, William and Dale, S.H. and Garcia-Alvarez, P. and Hevia, E. and Hogg, L.M. and Kennedy, A.R. and Mulvey, R.E. and O'Hara, Charles (2009) Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene. Angewandte Chemie, 48 (46). pp. 8675-8678. ISSN 0044-8249

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Abstract

Double role for sodium: Within a synergic sodium TMP-zincate reagent, sodium mediates the direct ortho-zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N,N-tetramethylethylenediamine.

ORCID iDs

Armstrong, D.R., Balloch, L., Clegg, William, Dale, S.H., Garcia-Alvarez, P., Hevia, E. ORCID logoORCID: https://orcid.org/0000-0002-3998-7506, Hogg, L.M., Kennedy, A.R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Mulvey, R.E. ORCID logoORCID: https://orcid.org/0000-0002-1015-2564 and O'Hara, Charles ORCID logoORCID: https://orcid.org/0000-0002-1691-1568;
  • Item type:Article
    ID code:18878
    Dates:
    Date
    Event
    2 November 2009
    Published
    Keywords:alkali metals, cooperative effects, metallacyclic compounds, metalation, zinc, Chemistry, Medicine(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Strathprints Administrator
    Date deposited:19 May 2010 10:54
    Last modified:20 Jan 2021 18:38
    URI:https://strathprints.strath.ac.uk/id/eprint/18878
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