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

Evan R. Judge; Keith O’Shaughnessy; Simon E. Lawrence; Stuart G. Collins; Anita R. Maguire

doi:10.1055/a-2348-5631

Synthesis, Table of Contents

Synthesis 2024; 56(24): 3752-3768
DOI: 10.1055/a-2348-5631

paper

Recent Advancements in the Chemistry of Diazo Compounds

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

Authors

Evan R. Judge

^aSchool of Chemistry, Analytical and Biological Chemistry Research Facility, SSPC, The SFI Research Centre for Pharmaceuticals, University College Cork, Cork, Ireland
Keith O’Shaughnessy

^aSchool of Chemistry, Analytical and Biological Chemistry Research Facility, SSPC, The SFI Research Centre for Pharmaceuticals, University College Cork, Cork, Ireland
Simon E. Lawrence

^aSchool of Chemistry, Analytical and Biological Chemistry Research Facility, SSPC, The SFI Research Centre for Pharmaceuticals, University College Cork, Cork, Ireland
Stuart G. Collins ∗

^aSchool of Chemistry, Analytical and Biological Chemistry Research Facility, SSPC, The SFI Research Centre for Pharmaceuticals, University College Cork, Cork, Ireland
Anita R. Maguire ∗

^aSchool of Chemistry, Analytical and Biological Chemistry Research Facility, SSPC, The SFI Research Centre for Pharmaceuticals, University College Cork, Cork, Ireland

^bSchool of Pharmacy, University College Cork, Cork, Ireland

Abstract

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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-halosulfonamides

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