Synthesis and reactivity of α-diazo-β-keto sulfonamides

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Date
2024-06-19
Authors
Maguire, Anita R.
Judge, Evan
O'Shaughnessy, Keith A.
Lawrence, Simon E.
Collins, Stuart G.
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Georg Thieme Verlag KG
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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%).
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Keywords
α-diazo-β-keto sulfonamides , Alkyne sulfonamide , Enamine , α-halosulfonamide
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
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