75421-81-7Relevant academic research and scientific papers
Regioselective and oxidant-free sulfinylation of indoles and pyrroles with sulfinamides
Ji, Yuan-Zhao,Zhang, Jin-Yu,Li, Hui-Jing,Han, Chunguang,Yang, Yi-Kun,Wu, Yan-Chao
, p. 4789 - 4800 (2019/05/24)
An unexpected time-controlled highly selective C3-or C2-sulfinylation of pyrroles with sulfinamides is reported for the first time. The sulfinylation of indoles with sulfinamides using this protocol is oxidant-free and can be performed under obviously more feasible conditions (1.2 equiv. of indoles, 10 min) in comparison with the precedent procedure (3-20 equiv. of indoles, 16-18 h, ammonium persulfate as oxidant, hv). A variety of functional groups were tolerated, and various C2-thioindoles and C2/3-thiopyrroles were obtained in moderate to excellent yields.
Visible-Light-Accelerated C?H Sulfinylation of Heteroarenes
Meyer, Andreas Uwe,Wimmer, Alexander,K?nig, Burkhard
supporting information, p. 409 - 412 (2016/12/30)
Heteroaromatic sulfoxides are a frequent structural motif in natural products, drugs, catalysts, and materials. We report a metal-free visible-light-accelerated synthesis of heteroaromatic sulfoxides from sulfinamides and peroxodisulfate. The reaction proceeds at room temperature with blue-light irradiation and allows the C?H sulfinylation of electron-rich heteroarenes, such as pyrroles and indoles. An electrophilic aromatic substitution mechanism is proposed based on the substrate scope, substitution selectivity, and competition experiments with different nucleophiles.
Synthesis and Rearrangement of 2-(Arylsulfinyl)- and 2-(Alkylsulfinyl)pyrroles
Carmona, Olga,Greenhouse, Robert,Landeros, Rosita,Muchowski, Joseph M.
, p. 5336 - 5339 (2007/10/02)
Pyrrole and N-methylpyrrole reacted with aryl- and alkylsulfinyl chlorides, at 0 deg C, to give the corresponding 2-sulfinylpyrroles as the major products only when contact of the products with the liberated hydrogen chloride was minimized or eliminated.If this precaution was not taken, the 3-sulfinylpyrroles were the principle products.In contrast, N-(phenylsulfinyl)succinimide (2a) reacted, at room temperature, with a variety of pyrroles to produce the 2-phenylsulfinyl compounds in good yields.The 2-(arylsulfinyl)- and 2-(alkylsulfinyl)pyrroles undergo a remarkably facile acid-promoted rearrangement to the isomeric 3-sulfinylpyrroles.This transposition is, at least in part, an intermolecular process as demonstrated by crossover experiments.
