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Regioselective Functionalization of Arenes Using Iron Triflimide Catalysis

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Here we present our development of the super Lewis acid, iron(III) triflimide as an activating agent of N-halo- and N-thioaryl succinimides for the regioselective functionalization of arenes. We also describe… Click to show full abstract

Here we present our development of the super Lewis acid, iron(III) triflimide as an activating agent of N-halo- and N-thioaryl succinimides for the regioselective functionalization of arenes. We also describe how the iron(III)-catalyzed halogenation reactions were further exploited by combination with copper(I)-catalyzed Ullmann-type coupling reactions for the development of one-pot, multistep processes, including intermolecular aryl C–H amination. This Account also illustrates intramolecular versions of these one-pot processes for the preparation of benzannulated heterocycles, as well as the application of these methods for the synthesis of biologically active compounds and natural products.1 Introduction2 Iron(III)-Catalyzed Halogenation of Arenes3 One-Pot Intermolecular Aryl C–H Amination4 One-Pot Intramolecular C–N, C–O, and C–S Bond-Forming Processes5 Iron(III)-Catalyzed Thioarylation of Arenes6 Synthesis of Phenoxathiins and Phenothiazines Using Lewis Acid and Lewis Base Catalysis7 Conclusions

Keywords: iron; one pot; iron iii; functionalization arenes; regioselective functionalization

Journal Title: Synlett
Year Published: 2023

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