Synthesis of cyclic sulfilimines and sulfoximines via copper mediated C(sp2)–H sulfanylation of benzylamines with a catalytic transient directing group
File(s)
Author(s)
Ma, Tsz Kan
Saejong, Peerawat
Or, King-Long
Begg, Callum
Bull, James
Type
Journal Article
Abstract
C–H Functionalization presents opportunities to streamline the synthesis of valuable molecular structures. This study details the development of a copper mediated, transient C(sp²)–H sulfanylation of benzylamines with a transient directing group (TDG). Subsequent oxidative cyclization forms novel cyclic sulfilimines and sulfoximines, emerging heterocyclic scaffolds with attractive properties for drug discovery. Crucially, sulfenamides were identified as effective sulfanylating reagents for the C–H sulfanylation with catalytic 2-hydroxynicotinaldehyde as the TDG. Unconventionally, sulfenamides provided a slow release of the essential sulfanyl radicals through a thermally induced homolytic cleavage of the N–S bond, supported by mechanistic studies including EPR spectroscopy and radical quenching experiments. The sulfide products were then readily diversified at sulfur and nitrogen including through cyclisation.
Date Issued
2025-08-02
Date Acceptance
2025-07-16
Citation
ChemistryEurope, 2025
ISSN
2751-4765
Publisher
Wiley
Journal / Book Title
ChemistryEurope
Copyright Statement
© 2025 The Author(s). ChemistryEurope published by Chemistry Europe and Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
License URL
Publication Status
Published online
Article Number
2500209
Date Publish Online
2025-08-02