One-pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water

Nickel-Catalyzed Reaction between Vinyl Azides and an Alkyl Sulfonyl Radical Generated from DMSO: Rapid Access to β-Keto Sulfones

“…34−37 Notably, a series of reactions using sulfonyl hydrazines as the source of sulfonyl radicals to react with vinyl azides for the preparation of β-keto sulfones have been reported. 28,29,38,39 In 2023, our group has developed a copper-catalyzed multicomponent cascade reaction for the synthesis of β-keto sulfones from vinyl azides, oxime esters, and Na 2 S 2 O 5 . 28 Although remarkable progress has been achieved in the reaction between sulfonyl radicals and vinyl azides, the use of DMSO as a source of alkyl sulfonyl radical has never been mentioned.…”

“…Vinyl azides as a crucial class of synthons have received extensive attention from organic chemists in chemical synthesis. − In this context, the addition reactions of vinyl azides with sulfonyl radicals are prominent, providing a reliable pathway to construct β-keto sulfones, enamines, phenanthridines, etc. (Scheme C). − Among them, β-keto sulfones are commonly employed as a critical synthetic building block in organic syntheses. − Notably, a series of reactions using sulfonyl hydrazines as the source of sulfonyl radicals to react with vinyl azides for the preparation of β-keto sulfones have been reported. ,,, In 2023, our group has developed a copper-catalyzed multicomponent cascade reaction for the synthesis of β-keto sulfones from vinyl azides, oxime esters, and Na 2 S 2 O 5 . Although remarkable progress has been achieved in the reaction between sulfonyl radicals and vinyl azides, the use of DMSO as a source of alkyl sulfonyl radical has never been mentioned.…”

Synthesis of α‐Sulfonyl Ketones through a Salicylic Acid‐Catalyzed Multicomponent Reaction Involving Arylsulfonation and Oxidation

“…Most of these methods rely on the reaction of arylsulfonyl radicals with alkenes, [23][24][25][26][27][28][29][30][31][32][33] alkynes, [34][35][36][37] silyl enol ethers, [38] enol acetates, [39] enol phosphates, [40] enamides, [41] vinyl azide, [42][43] atropic acids, [44] or hydrazones. [45] As the source of the arylsulfonyl radicals, sulfonyl chlorides, [23][24][25]34,[38][39] sodium sulfinates, [26][27][35][36]43,45] arylsulfinic acid, [28][29]37,40] sulfonyl hydrazides [30][31][32]41,44] or the combination of sulfonyl chlorides and hydrazine, [42] and S-phenyl benzenesulfonothioate [33] have been employed. Depending on the reagents used, the reactions can be either photocatalyzed, [23]…”

“…[45] As the source of the arylsulfonyl radicals, sulfonyl chlorides, [23][24][25]34,[38][39] sodium sulfinates, [26][27][35][36]43,45] arylsulfinic acid, [28][29]37,40] sulfonyl hydrazides [30][31][32]41,44] or the combination of sulfonyl chlorides and hydrazine, [42] and S-phenyl benzenesulfonothioate [33] have been employed. Depending on the reagents used, the reactions can be either photocatalyzed, [23][24]29,34,39,44] metalcatalyzed, [27,[32][33]35,38,42,45] or completely metalfree. [25][26]28,[30][31][36][37][40][41]43] Through the initial work of Willis, Wu, and others, [46]…”