Electrochemical synthesis of α-thiocyanato-α-carbonyl sulfoxonium ylides

Synthesis of Sulfo(xo)nium Diacylmethylides

“…Generally, the alkylation of sulfides with α ‐haloketones and subsequent deprotonation of the generated sulfo(xo)nium salts with strong bases yield sulfo(xo)nium monoacylmethylides in excellent yields [14] . The acylation of sulfo(xo)nium methylides with carboxylic acid derivatives [14a,15] and the modification of sulfo(xo)nium monoacylmethylides with arynes [16] and (hetero)aryl halides [17] for the (hetero)arylations, thiosulfonates for the alkyl/arylthiolation, [18] NaBr/MgCl 2 for the chlorination and bromination, [19] KSCN for the thiocyanation [20] or TsCN for the cyanation, [21] are also useful strategies for the preparation of new sulfo(xo)nium monoacylmethylides.…”

Synthesis of α-cyanato-α′-carbonyl sulfoxonium ylides in water

“…16 Zhang's group focused on the electrochemical synthesis of bis-substituted sulfoxonium ylides. 17,18 They successfully achieved electrochemically promoted C-H bond chlorination and thiocyanation of mono-substituted sulfoxonium ylides, enabling the gram-scale production of these two novel types of sulfoxonium ylides. Subsequent mechanistic studies have confirmed the involvement of a radical pathway in these reactions.…”