Regioselective functionalization of arenes using iron triflimide catalysis

Dodds, A. C., Waddell, L. J.N. and Sutherland, A. (2023) Regioselective functionalization of arenes using iron triflimide catalysis. Synlett, 34(16), pp. 1852-1865. (doi: 10.1055/s-0042-1751445)

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.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew and Waddell, Mr Lachlan and Dodds, Miss Amy
• Authors: Dodds, A. C., Waddell, L. J.N., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Synlett
• Publisher: Thieme Publishing
• ISSN: 0936-5214
• ISSN (Online): 1437-2096
• Published Online: 26 April 2023
• Copyright Holders: Copyright © 2023 Thieme
• First Published: First published in Synlett 34(16): 1852-1865
• Publisher Policy: Reproduced with the permission of the Publisher

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
312561		EPSRC DTP 2020/21	Christopher Pearce	Engineering and Physical Sciences Research Council (EPSRC)	EP/T517896/1	Research and Innovation Services