The synthesis of trifluoromethylselenolated aromatic molecules via an auxiliary-assisted, palladium catalyzed, C-H bonds functionalization with trifluoromethyl tolueneselenosulfonate as reagent is described. The mono- or bis-products can be preferentially formed. Some mechanistic investigations were realized to better understand the reaction. This methodology was also extended to fluoroalkylselenyl groups.
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Direct trifluoromethylselenolations of electron-rich (hetero)aromatic rings with -trifluoromethylselenolating saccharin.
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A novel, easily synthesizable, shelf-stable electrophilic trifluoromethylselenolating reagent, -trifluoromethylselenosaccharin, has been developed. This reagent can be synthesized in good yield by a two-step one-pot reaction from BnSeCF, SOCl, and silver saccharin. -Trifluoromethylselenosaccharin proves to be an efficient trifluoromethylselenolating reagent, enabling the direct trifluoromethylselenolation of various electron-rich aromatic and heteroaromatic rings under mild reaction conditions.
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School of Materials Science and Engineering and School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 122 Luoshi Road, Wuhan 430070, China.
Visible-light-induced decarboxylative trifluoromethylselenolation of (hetero)aromatic carboxylic acids with [MeN][SeCF], oxidant, and catalysts afforded a variety of (hetero)aryl trifluoromethyl selenoethers in good yields. The reaction might involve a radical process, which generated (hetero)aryl radicals from the stable (hetero)aromatic carboxylic acids via oxidative decarboxylation with NFSI as the oxidant, [di-Bu-Mes-Acr-Ph][BF] as the photocatalyst, and 1,1'-biphenyl as the cocatalyst. Both catalysts had a decisive influence on the reaction.
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The synthesis of trifluoromethylselenolated aromatic molecules via an auxiliary-assisted, palladium catalyzed, C-H bonds functionalization with trifluoromethyl tolueneselenosulfonate as reagent is described. The mono- or bis-products can be preferentially formed. Some mechanistic investigations were realized to better understand the reaction.
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Trifluoromethylselenylated compounds are emergent compounds with interesting physicochemical properties that still suffer from a lack of efficient synthetic methods. We recently developed an efficient one-pot strategy to generate in situ CF₃SeCl and use it in various reactions. Herein, we continue our study of the reactivity scope of this preformed reagent.
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