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A one-pot, two-stage synthesis of diaryl sulfonamides using sequential iron and copper catalysis has been developed. Regioselective para-iodination of activated arenes by the super Lewis acid, iron triflimide and N-iodosuccinimide (NIS), was followed by a copper(I)-catalyzed N-arylation reaction. The process was found to be applicable for the coupling of a range of anisoles, anilines and acetanilides with primary sulfonamides and was used for the one-pot synthesis of biologically important compounds

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