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Aryne Insertion into σ Bonds
Author(s) -
Asamdi Manjoorahmed,
Chikhalia Kishor H.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700284
Subject(s) - aryne , chemistry , trimethylsilyl , ring (chemistry) , benzene , aryl , catalysis , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , alkyl
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.