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Synthesis 2024; 56(24): 3752-3768
DOI: 10.1055/a-2348-5631
DOI: 10.1055/a-2348-5631
paper
Recent Advancements in the Chemistry of Diazo Compounds
Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides
The authors would like to acknowledge the Irish Research Council (IRC; E. J.: GOIPG/2020/369), the Higher Education Authority (HEA; COVID-19 Related Research Costed Extension to E. J.), the SSPC, the SFI Research Centre for Pharmaceuticals supported by Science Foundation Ireland (SFI) and co-funded under the European Regional Development Fund (SFI SSPC2 12/RC/2275, SFI SSPC3 Pharm5 12/RC/2275_2, and SFI 15/RI/3221), for funding. This publication has emanated from research supported in part by a grant from Science Foundation Ireland Research Infrastructure Programme under grant numbers 15/RI/3221 and 21/RI/9705. X-ray crystallography was made possible through SFI funding (05/PICA/B802/EC07).
Abstract
Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range of products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-oxo sulfones. Use of copper(II) triflate (5 mol%) led to the isolation of a series of alkynesulfonamides (up to 12% yield) and enamines (up to 64% yield). Use of copper(II) chloride (5 mol%) led to the formation, in addition, of α-halosulfonamides; use of stoichiometric amounts of copper(II) chloride/bromide enabled facile halogenation of the β-keto sulfonamide to form α-halosulfonamides (up to 63% yield).
Keywords
C–H insertion - diazo compounds - copper catalysis - alkynesulfonamides - α-halosulfonamidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2348-5631. The SI includes details of preparation and characterisation of methanesulfonamides 3a–f, 4a–d, and β-keto sulfonamides 2a–h and 1H and 13C NMR spectra of α-diazo-β-keto sulfonamides 1a–h, alkynesulfonamides 5a–e,g,h, enamines 6a–e,g,h, and α-halosulfonamides 7a–d,f,g and 11a,c.
- Supporting Information
Publication History
Received: 24 May 2024
Accepted after revision: 19 June 2024
Accepted Manuscript online:
19 June 2024
Article published online:
08 August 2024
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