75421-91-9Relevant academic research and scientific papers
Efficient Synthesis of 3-(Arenesulfinyl)indoles in Water
Ji, Y. Z.,Li, H. J.,Liu, Y.,Wu, Y. C.,Zhang, Z. Y.
, p. 831 - 841 (2021/06/12)
Abstract: The first example of the sulfinylation of indoles with arylsulfinamides in water in the presence of trifluoroacetic acid as a promoter is described. The reaction occurs smoothly at room temperature under environmentally benign conditions without any catalyst, additive, ligand, or organic solvent. The developed sulfoxide synthetic protocol is attractive due to the use of water as the solvent and provides a novel and efficient route to a wide range of functionalized diaryl sulfoxides.
TMSOTf-Promoted Sulfinylation of Electron-Rich Aromatics with Sodium Arylsulfinates
Ji, Yuan-Zhao,Li, Hui-Jing,Wu, Yan-Chao,Xie, Li-Jun,Yang, Hao-Ran,Zhang, Zheng-Yan
, p. 349 - 354 (2020/02/27)
A new transition-metal-free route for the direct sulfinylation of electron-rich aromatics with sodium arylsulfinates in the presence of TMSOTf is reported. Various electron-rich aromatics, including pyrroles, thiophenes, indoles, and electron-rich arenes, with sodium arylsulfinates are converted into the corresponding sulfoxides in moderate to excellent yields. This protocol possesses many advantages such as readily available and stable starting materials, broad substrate scopes, and transition-metal-free reaction conditions.
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.
A sulfenylation reaction: Direct synthesis of 3-arylsulfinylindoles from arylsulfinic acids and indoles in water
Miao, Tao,Li, Pinhua,Zhang, Yicheng,Wang, Lei
supporting information, p. 832 - 835 (2015/03/18)
A novel and efficient electrophilic sulfenylation of indoles with arylsulfinic acids is realized. The reaction utilizes readily available starting materials in water under catalyst- and additive-free conditions, providing an alternative and attractive approach to 3-arylsulfinylindoles with high yields. Preliminary mechanistic investigation suggested that the reaction is through an electrophilic substitution process.
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.
