Electrosynthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates mediated by NH4I

Disulfides as versatile starting reagents: effective sulfonylation of alkenes with disulfides under electrochemical conditions

“…[38][39][40][41] In some cases, thiols dimerization is a side process, and the formed disulfides do not enter the sulfenylation reaction, which takes place in the case of thiols usage. [42][43][44] Sulfonylation often goes through the oxidative generation of sulfonyl radicals from sulfinic acids and their salts, [45][46][47][48] as well as sulfonyl hydrazides [49][50][51][52] (Scheme 1b).…”

Decatungstate-Catalyzed Photochemical Synthesis of Enaminones from Vinyl Azides and Aldehydes

“…As a continuation of our studies of the addition of radicals to vinyl azides, − we decided to study how these compounds behave under visible light irradiation in the presence of TBADT. The main feature of vinyl azides is that the addition of radical species to the terminal carbon atom of their CC bond leads to the release of N 2 and the formation of iminyl radicals. − The latter can be further transformed into enamines ,,,− or ketones − or can be subjected to intramolecular cyclization − or homocoupling and heterocoupling. ,, Electrochemical and Cu-catalyzed hydroacylation of vinyl azides via decarboxylative generation of acyl radical from α-ketoacids was also reported. Vinyl azides are prone to degradation to azirines by UV or even visible light irradiation, which makes the search of an effective method for their photochemical functionalization quite challenging.…”

Electrochemical Decarbonylative Aminosulfonylation of Alkynes with Sulfinates and N-(Formyl)anilides

“…Despite the fact that numerous approaches have been developed recently, variously functionalized vinyl sulfones are still hardly available. Therefore, synthesis of polyfunctional derivatives attracts much attention; for instance, N -unsubstituted enaminosulfones could be obtained electrochemically , or photocatalytically from vinyl azides. Both alkynes and sulfinates are widely used in free radical transformations.…”