Journal article
Synthesis, functionalization, and reactivity of vinyl sulfondiimidamides
- Abstract:
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Acrylamides are the dominant electrophilic warheads used in bioactive covalent inhibitors. A limitation of acrylamides, and related unsaturated sulfonamides, is the narrow scope to modulate their electrophilicity, and hence reactivity, through simple structural modification. Here, we show that vinyl sulfondiimidamides are effective electrophilic motifs for reaction with both sulfur- and nitrogenbased biologically relevant nucleophiles. We demonstrate that the electrophilicity of these new reagents can be tuned through variation of the imidic N-substituents. Vinyl sulfondiimidamides are prepared via a short sequence that features a Cope elimination as the key alkene-forming step. A broad range of N-substituents can be installed.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 1.4MB, Terms of use)
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- Publisher copy:
- 10.1002/anie.9885717
Authors
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Article number:
- e9885717
- Publication date:
- 2026-03-28
- Acceptance date:
- 2026-03-12
- DOI:
- EISSN:
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1521-3773
- ISSN:
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1433-7851
- Language:
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English
- Keywords:
- Pubs id:
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2388056
- Local pid:
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pubs:2388056
- Deposit date:
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2026-03-11
- ARK identifier:
Terms of use
- Copyright holder:
- Rodden et al.
- Copyright date:
- 2026
- Rights statement:
- © 2026 The Author(s). Angewandte Chemie International Edition published by 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.
- Licence:
- CC Attribution (CC BY)
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