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

Synthesis Pub Date : 2024-08-08 DOI:10.1055/a-2348-5631
Evan R. Judge, Keith O’Shaughnessy, Simon E. Lawrence, Stuart G. Collins, Anita R. Maguire
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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).

Abstract Image

α-Diazo-β-keto 磺酰胺的合成与反应活性
铜介导的 α-偶氮-β-酮基磺酰胺反应产生了一系列产物,包括炔基磺酰胺、烯胺和 α-卤代磺酰胺,在任何反应中都没有证据表明分子内 C-H 插入,这与可比的 α-偶氮-β-氧代砜的反应活性形成鲜明对比。使用三酸铜(II)(5 摩尔%)可以分离出一系列炔磺酰胺(收率高达 12%)和烯胺(收率高达 64%)。使用氯化铜(II)(5 mol%)还可生成 α-卤代磺酰胺;使用等量的氯化铜/溴化物可使 β-酮基磺酰胺简单卤化,生成 α-卤代磺酰胺(收率高达 63%)。
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