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Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications.

Authors
  • Suleymanov, Abdusalom A1
  • Severin, Kay1
  • 1 Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015, Lausanne, Switzerland. , (Switzerland)
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
Mar 22, 2021
Volume
60
Issue
13
Pages
6879–6889
Identifiers
DOI: 10.1002/anie.202011031
PMID: 33142011
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

Aromatic compounds containing triazenyl groups (N3 RR') have a profound impact on synthetic organic and medicinal chemistry. In contrast, the chemistry of vinyl and alkynyl triazenes was a largely uncharted territory until recently. The situation has changed over the last five years, and it has become apparent that vinyl and alkynyl triazenes are highly interesting compounds with a unique reactivity. The electron-donating properties of the triazenyl group provide alkynyl triazenes with an ynamide-like reactivity, which can be exploited in reactions of the triple bond. Vinyl triazenes, on the other hand, can be used for electrophilic vinylation reactions. The foundation for this new triazene chemistry are synthetic pathways which allow preparing vinyl and alkynyl triazenes in few steps from readily available starting materials. In this Minireview, we summarize recent developments in this area. © 2020 Wiley-VCH GmbH.

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