Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…Our research group 74 successfully demonstrated a convenient and metal-free protocol for the highly regioselective sulfonylation of NH -1,2,3-triazoles with sodium sulfinates. A range of disubstituted NH -1,2,3-triazoles were readily sulfonylated with various arylsulfinates in the presence of molecular iodine.…”

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

“…The formation of sulfonyl radical from homolysis of sulfonyl iodide was also proposed in the sulfonylation of NH‐1,2,3‐triazoles with sodium sulfinates (Scheme 54). [65] …”

“…The formation of sulfonyl radical from homolysis of sulfonyl iodide was also proposed in the sulfonylation of NH-1,2,3-triazoles with sodium sulfinates (Scheme 54). [65] An oxidative coupling of NH-sulfoximines and arylsulfinates catalyzed by of I 2 and H 2 O 2 for the preparation of N-sulfonyl sulfoximines was reported by Zeng group. [66] This reaction could be conducted at room temperature in water.…”

NaI‐Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants

“…Molecular iodine was recognized as a transition metal surrogate to catalyze, or as a selective environmentally friendly oxidant, to perform a wide range of coupling reactions of sodium sulfinates with, e.g. imidazopyridines, alkynes, cinnamic acids, 1,3‐dicarbonyl compounds, enol acetates, benzotriazoles and NH‐1,2,3‐triazoles etc. Recently, Yotphan et al disclosed an efficient iodine‐catalyzed, sodium percarbonate participated oxidative amination of sodium sulfinates whereby sulfonamides were prepared in good yields.…”