An efficient palladium-catalyzed region-selective C7-trifluoromethylation of indolines using commercially available Umemoto's reagent was reported. The reaction utilizing Umemoto's reagent as CF radical precursor, pyrimidine as a removable directing group, Pd(II) as a catalyst, and Cu(II) as an oxidant furnished the required products with excellent regioselectivities and good yields. The present strategy has good region-selectivity, broad substrate scope, and scale-up application. Additionally, the present method was underlined by the direct C-1 trifluoromethylation of carbazoles. Furthermore, C7 trifluoromethylated indole can also be easily obtained via Pd-catalyzed direct C-7 trifluoromethylation/oxidation/deprotection sequential reactions.
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Pd-Catalyzed Direct C7 Trifluoromethylation of Indolines with Umemoto's Reagent.
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An efficient palladium-catalyzed region-selective C7-trifluoromethylation of indolines using commercially available Umemoto's reagent was reported. The reaction utilizing Umemoto's reagent as CF radical precursor, pyrimidine as a removable directing group, Pd(II) as a catalyst, and Cu(II) as an oxidant furnished the required products with excellent regioselectivities and good yields. The present strategy has good region-selectivity, broad substrate scope, and scale-up application.
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A visible-light-promoted research protocol for constructing dihydropyrido[1,2-]indolone skeletons is herein described proceeding through a cascade cyclization mediated by trifluoromethyl radicals. This method allows the efficient synthesis of various indole derivatives without the need of photocatalysts or transition-metal catalysts. Mechanism experiments indicate that the process involves a radical chain process initiated by the homolysis of Umemoto's reagent.
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