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

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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 1521-3773 (https://doi.org/10.1002/anie.200904506)

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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;
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