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Relevant academic research and scientific papers

Transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles with sodium trifluoromethanesulfinates in ionic liquids

An acid-promoted protocol has been developed to achieve the transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles using sodium trifluoromethanesulfinates in an imidazolium-based ionic liquid ([Hmim]Br). [Hmim]Br not only acts as a recyclable solvent, but also as the reductant in this transformation. The advantages of this chemistry include simple operation, use of a recyclable solvent, avoidance of transition-metal and phosphorus, and gram-scale synthesis.

Green indole compound vulcanization method with triphosgene as reducing agent

The invention discloses a green indole compound vulcanization method with triphosgene as a reducing agent. The method comprises the following steps: by taking indole and a derivative thereof as substrate, fluomethane sodium methanesulfinate, methyl sodium methanesulfinate, cyclopropyl sodium methanesulfinate or aryl sodium methanesulfinate as a vulcanization agent, triphosgene as a reducing agent,and acetonitrile as a solvent, stirring for 2 hours in an ice bath, carrying out TLC (Thin Layer Chromatography) reaction tracking, and after sufficient reactions are completed, carrying out column chromatography isolation, so as to obtain various indole vulcanization compounds. By adopting the method disclosed by the invention, the triphosgene is adopted as the reaction reducing agent, thiophenol and dithioether with serious smell is avoided, an expensive electrophilic trifluoromethyl sulfide reagent is avoided, and a phosphorous reducing agent which can do harm to the environment can be also avoided. Till now, the indole vulcanization method is not reported yet, the preparation method is simple and convenient, low in cost and high in yield, products can be directly prepared without anytransition metal catalyst or aid, and very high practical popularization values can be achieved.

Method for preparing trifluoro-methylmercapto-substituted indole compound

The invention discloses a method for preparing a trifluoro-methylmercapto-substituted indole compound. The method comprises the following step: by taking trifluoro-methyl sodium sulfonate as a trifluoro-methylmercapto source and triphenylphosphine as a reducing agent, under the action of a visible light catalyst eosin Y, and enabling a substituted indole compound, the trifluoro-methyl sodium sulfonate and triphenylphosphine to react with N-chloro-o-phthalimide, thereby obtaining the trifluoro-methylmercapto-substituted indole compound. The method disclosed by the invention is simple, a trifluoro-methylmercapto reagent used in the method is low in toxicity, and no heating is needed in the preparation process, so that the energy can be saved, the environment can be protected, and direct trifluoro-methylmercapto reaction of a 3-position C (sp2)-H bond of an indole compound is achieved.

Selective Trifluoromethylthiolation and Trifluoromethylsulfinylation of Indoles with Sodium Trifluoromethanesulfinate Promoted by Phosphorus Reagents

Direct trifluoromethylthiolation and trifluoromethylsulfinylation reactions by using sodium trifluoromethanesulfinate were promoted by different phosphorus reagents to selectively occur under mild and transition-metal-free conditions. In the presence of phosphorus trichloride, sodium trifluoromethanesulfinate readily underwent a reaction with indole and its derivatives in N,N-dimethylformamide (DMF) at room temperature to give 3-trifluoromethylthiolated products in good yields. Trifluoromethylsulfinylation reactions, however, occurred at the C-3 position when phosphorus oxychloride was used to give the corresponding sulfoxides in high yields. This protocol was further extended to the use of other sodium perfluoroalkanesulfinates.

Direct trifluoromethylthiolation and perfluoroalkylthiolation of C(sp2)-H bonds with CF3SO2Na and RfSO2Na

A new method for CF3SO2Na-based direct trifluoromethylthiolation of C(sp2)-H bonds has been developed. CF3SSCF3 is generated in situ from cheap and easy-to-handle CF3SO2Na, and in the presence of CuCl can be used for electrophilic trifluoromethylthiolation of indoles, pyrroles, and enamines. The method has been extended to perfluoroalkylthiolation reactions using RfSO2Na. Easy to handle: A new method for CF3SO2Na-based direct trifluoromethylthiolation of C(sp2)-H bonds has been developed. CF3SSCF3 is generated in situ from cheap and easy-to-handle CF3SO2Na, and in the presence of CuCl can be used for electrophilic trifluoromethylthiolation of indoles, pyrroles, and enamines. The method has been extended to perfluoroalkylthiolation reactions using RfSO2Na.