An Aminative Rearrangement of O-(Arenesulfonyl)hydroxylamines: Facile Access to ortho-Sulfonyl Anilines.
Arene Amination
Ion-Pairing
Non-Covalent Interactions
Radical Reactions
Regioselectivity
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
15 Aug 2022
15 Aug 2022
Historique:
received:
17
03
2022
pubmed:
16
6
2022
medline:
16
6
2022
entrez:
15
6
2022
Statut:
ppublish
Résumé
Ortho-sulfonyl anilines are important building blocks for a range of applications. We report the discovery of an aromatic rearrangement reaction of O-(arenesulfonyl)hydroxylamines which leads directly to ortho-sulfonyl anilines through formation of a new C-N bond with excellent levels of regiocontrol for the ortho position(s) over all others. We establish that the rearrangement is proceeding through an intermolecular mechanism and propose that the regiocontrol observed is the result of attractive non-covalent interactions occurring during the C-N bond-forming step. Importantly, this method is complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that can be obtained and it is also applicable to O-(benzylsulfonyl) hydroxylamines.
Identifiants
pubmed: 35703005
doi: 10.1002/anie.202204025
pmc: PMC9546328
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202204025Subventions
Organisme : The Royal Society
ID : URF\R\191003
Organisme : The Royal Society
ID : RGF\EA\180005
Organisme : Engineering and Physical Sciences Research Council
ID : EP/S03269X/1
Organisme : H2020 European Research Council
ID : 757381
Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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