Regioselective Functionalization of Arenes Using Iron Triflimide Catalysis

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

Publikationsverlauf

Eingereicht: 02. Februar 2023

Angenommen nach Revision: 21. März 2023

Artikel online veröffentlicht:
26. April 2023

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