Access to this article is restricted until 12 months after publication by request of the publisher. Restriction lift date: 2025-06-19
Synthesis and reactivity of α-diazo-β-keto sulfonamides
| dc.check.date | 2025-06-19 | en |
| dc.check.info | Access to this article is restricted until 12 months after publication by request of the publisher | en |
| dc.contributor.author | Maguire, Anita R. | en |
| dc.contributor.author | Judge, Evan | en |
| dc.contributor.author | O'Shaughnessy, Keith A. | en |
| dc.contributor.author | Lawrence, Simon E. | en |
| dc.contributor.author | Collins, Stuart G. | en |
| dc.contributor.funder | Science Foundation Ireland | en |
| dc.contributor.funder | Irish Research Council | en |
| dc.contributor.funder | Higher Education Authority | en |
| dc.contributor.funder | Synthesis and Solid State Pharmaceutical Centre | en |
| dc.contributor.funder | European Regional Development Fund | en |
| dc.date.accessioned | 2024-07-15T09:25:16Z | |
| dc.date.available | 2024-07-15T09:25:16Z | |
| dc.date.issued | 2024-06-19 | en |
| dc.description.abstract | Copper mediated reactions of α-diazo-β-keto sulfonamides 1 leads to a range of products including the alkyne sulfonamides 5, the enamines 6, and the α-halosulfonamides 7 and 11 with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-keto sulfones. Use of copper(II) triflate (5 mol%) led to isolation of a series of alkyne sulfonamides 5 (up to 12%) and enamines 6 (up to 64%). Use of copper(II) chloride (5 mol%) formed, in addition, the α-halosulfonamides 7; use of stoichiometric amounts of copper(II) chloride/bromide enables facile halogenation of the β-keto sulfonamide to form the α-halosulfonamides 7 and 11 (up to 63%). | en |
| dc.description.sponsorship | Irish Research Council (GOIPG/2020/369); Science Foundation Ireland (SFI SSPC3 Pharm5 12/RC/2275_2; 05/PICA/B802/EC07) | en |
| dc.description.status | Peer reviewed | en |
| dc.description.version | Accepted Version | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.citation | Maguire, A. R., Judge, E., O'Shaughnessy, K. A., Lawrence, S. E. and Collins, S. G. (2024) 'Synthesis and reactivity of α-diazo-β-keto sulfonamides', Synthesis. https://doi.org/10.1055/a-2348-5631 | en |
| dc.identifier.doi | https://doi.org/10.1055/a-2348-5631 | en |
| dc.identifier.eissn | 1437-210X | en |
| dc.identifier.issn | 0039-7881 | en |
| dc.identifier.journaltitle | Synthesis | en |
| dc.identifier.uri | https://hdl.handle.net/10468/16122 | |
| dc.language.iso | en | en |
| dc.publisher | Georg Thieme Verlag KG | en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Equipment Call/05/PICA/B802/EC07/IE/Single Crystal X-Ray Diffractometer/ | en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ | en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/15/RI/3221/IE/Process Flow Spectroscopy (ProSpect); Advanced Reaction Understanding using Flow Nuclear Magnetic Resonance (NMR) and Infrared (IR) Spectroscopies, with On-Line Ultra-Performance Liquid Chromatography (UPLC) and Mass Spectrometry (MS)/ | en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/15/RI/3221/IE/Process Flow Spectroscopy (ProSpect); Advanced Reaction Understanding using Flow Nuclear Magnetic Resonance (NMR) and Infrared (IR) Spectroscopies, with On-Line Ultra-Performance Liquid Chromatography (UPLC) and Mass Spectrometry (MS)/ | en |
| dc.relation.project | info:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/21/RI/9705/IE/Fast reaction kinetics in NMR Spectroscopy - FaNS/ | en |
| dc.relation.project | 5/PICA/B802/EC07 | en |
| dc.rights | © 2024, Thieme. All rights reserved. | en |
| dc.subject | α-diazo-β-keto sulfonamides | en |
| dc.subject | Alkyne sulfonamide | en |
| dc.subject | Enamine | en |
| dc.subject | α-halosulfonamide | en |
| dc.title | Synthesis and reactivity of α-diazo-β-keto sulfonamides | en |
| dc.type | Article (peer-reviewed) | en |
Files
Original bundle
1 - 1 of 1
Loading...
- Name:
- Manuscript for Cora July 2024.pdf
- Size:
- 477.13 KB
- Format:
- Adobe Portable Document Format
- Description:
- Accepted Version
License bundle
1 - 1 of 1
Loading...
- Name:
- license.txt
- Size:
- 2.71 KB
- Format:
- Item-specific license agreed upon to submission
- Description: