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Intermolecular Aryl C-H Amination through Sequential Iron and Copper Catalysis.

Mohamed A B Mostafa¹, Ewen D D Calder¹, Daugirdas T Racys¹

¹WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, University Avenue, Glasgow, G12 8QQ, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|December 6, 2016

Summary

This study introduces a new, efficient method for para-amination of activated arenes using iron and copper catalysts. The process is regioselective, works in one pot, and avoids protecting groups for diverse aryl compounds.

Keywords:

amination bromination copper catalysis cross-coupling iron catalysis

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Developing efficient and regioselective methods for C-H functionalization is crucial in organic synthesis.
Aromatic amination reactions are fundamental transformations for creating valuable nitrogen-containing compounds.

Purpose of the Study:

To develop a mild, efficient, and regioselective method for the para-amination of activated arenes.
To establish a one-pot, two-step procedure for coupling aromatic C-H bonds with amines.

Main Methods:

Utilized a combination of iron and copper catalysis for the amination reaction.
Employed iron(III) triflimide as a Lewis acid for bromination, followed by copper(I)-catalyzed N-arylation.
Applied the method to anisole-, phenol-, aniline-, and acetanilide-type aryl compounds.

Main Results:

Achieved regioselective para-amination of activated arenes.
Successfully coupled a diverse range of aryl compounds with non-activated amines.
Demonstrated the utility of the method without requiring protecting-group manipulations on arene substrates.

Conclusions:

The developed method offers a mild, efficient, and regioselective route to para-aminated arenes.
The one-pot, two-step procedure simplifies the synthesis of complex aromatic amines.
This approach is broadly applicable to various activated aryl substrates, using them as the limiting reagent.