Rapid and Scalable Halosulfonylation of Strain-Release Reagents.
Bicyclic Compounds
Bioisosteres
Small-Ring Systems
Strained Molecules
Sulfonylation
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:
16 01 2023
16 01 2023
Historique:
received:
14
09
2022
pubmed:
14
10
2022
medline:
12
1
2023
entrez:
13
10
2022
Statut:
ppublish
Résumé
Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve the physicochemical properties of drug and agrochemical candidates, are limited. Here we report a solution to this challenge: a one-pot halosulfonylation of [1.1.1]propellane, [3.1.1]propellane and bicyclo[1.1.0]butanes that proceeds under practical, scalable and mild conditions. The sulfonyl halides used in this chemistry feature aryl, heteroaryl and alkyl substituents, and are conveniently generated in situ from readily available sulfinate salts and halogen atom sources. This methodology enables the synthesis of an array of pharmaceutically and agrochemically relevant halogen/sulfonyl-substituted bioisosteres and cyclobutanes, on up to multidecagram scale.
Identifiants
pubmed: 36226350
doi: 10.1002/anie.202213508
pmc: PMC10100009
doi:
Substances chimiques
Indicators and Reagents
0
Butanes
0
Halogens
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202213508Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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