Directed meta-Metalation Using Alkali-Metal-Mediated Zincation

Move over directed ortho‐metalation, here comes directed meta‐metalation. The unprecedented meta‐zincation of two anilides by a synergic mixed sodium/zinc dialkyl–amide base is presented. The orientation of the deprotonation of the anilides is remarkably switched to the meta site using this heterome...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2006-06, Vol.45 (23), p.3775-3778
Main Authors: Armstrong, David R., Clegg, William, Dale, Sophie H., Hevia, Eva, Hogg, Lorna M., Honeyman, Gordon W., Mulvey, Robert E.
Format: Article
Language:English
Subjects:
anilides
deprotonation
metalation
sodium
zincation
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Summary:Move over directed ortho‐metalation, here comes directed meta‐metalation. The unprecedented meta‐zincation of two anilides by a synergic mixed sodium/zinc dialkyl–amide base is presented. The orientation of the deprotonation of the anilides is remarkably switched to the meta site using this heterometallic mixed‐metal system.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200600720