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Synthesis
DOI: 10.1055/a-2348-5631
paper

Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Anita R Maguire 
1   Chemistry, University College Cork, Cork, Ireland (Ringgold ID: RIN8795)
,
Evan Judge 
2   School of Chemistry, University College Cork, Cork, Ireland (Ringgold ID: RIN8795)
,
Keith A O'Shaughnessy 
1   Chemistry, University College Cork, Cork, Ireland (Ringgold ID: RIN8795)
,
Simon E. Lawrence
3   School of Chemistry, University College Cork National University of Ireland, Cork, Ireland (Ringgold ID: RIN8795)
,
Stuart G. Collins 
1   Chemistry, University College Cork, Cork, Ireland (Ringgold ID: RIN8795)
› Author AffiliationsSupported by: Science Foundation Ireland 05/PICA/B802/EC07,21/RI/9705,SFI 15/RI/3221 ,SFI SSPC2 12/RC/2275,SFI SSPC3 Pharm5 12/RC/2275_2
Supported by: Higher Education Authority COVID-19 related research costed extension
Supported by: Irish Research Council GOIPG/2020/369
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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%).



Publication History

Received: 24 May 2024

Accepted after revision: 19 June 2024

Accepted Manuscript online:
19 June 2024

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