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Aryne Insertion into σ Bonds

The synthesis of aryne intermediates from ortho‐(trimethylsilyl)aryl triflates by employing a fluoride source, first reported by Kobayashi′s group, has provided a new avenue for the simultaneous construction of two sigma bonds on a benzene ring by inserting an aryne into the sigma bond in a more‐con...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2017-10, Vol.6 (10), p.1331-1348
Main Authors: Asamdi, Manjoorahmed, Chikhalia, Kishor H.
Format: Article
Language:English
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Summary:The synthesis of aryne intermediates from ortho‐(trimethylsilyl)aryl triflates by employing a fluoride source, first reported by Kobayashi′s group, has provided a new avenue for the simultaneous construction of two sigma bonds on a benzene ring by inserting an aryne into the sigma bond in a more‐convenient manner. The generation of ortho‐substituted benzenes through aryne intermediates offers a potent scaffold for the synthesis of bioactive heterocyclic compounds, ligands, and natural products. The main aim of this Focus Review is to highlight the application of Kobayashi′s aryne precursor to the one‐pot synthesis of ortho‐substituted benzenes. Examples include transformations that employ transition‐metal catalysis and those that do not. Double trouble: The application of Kobayashi′s aryne precursor for the simultaneous construction of two sigma bonds on an arene ring and its importance in organic chemistry are described. Examples include transformations that employ transition‐metal catalysis and those that do not.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700284