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 Introduction
2 Iron(III)-Catalyzed Halogenation of Arenes
3 One-Pot Intermolecular Aryl C–H Amination
4 One-Pot Intramolecular C–N, C–O, and C–S Bond-Forming Processes
5 Iron(III)-Catalyzed Thioarylation of Arenes
6 Synthesis of Phenoxathiins and Phenothiazines Using Lewis Acid and Lewis Base Catalysis
7 Conclusions
Key words
iron and copper catalysis - halogenation - thioarylation - Ullmann coupling - heterocycle
synthesis
