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CC BY 4.0 · Synthesis 2021; 53(07): 1213-1228
DOI: 10.1055/s-0040-1705999
short review

Modification of Azobenzenes by Cross-Coupling Reactions

Melanie Walther 
a   University of Bremen, Institute for Analytical and Organic Chemistry, Leobener Straße 7, 28359 Bremen, Germany
b   MAPEX Center for Materials and Processes, Bibliothekstraße 1, 28359 Bremen, Germany
,
Waldemar Kipke 
a   University of Bremen, Institute for Analytical and Organic Chemistry, Leobener Straße 7, 28359 Bremen, Germany
b   MAPEX Center for Materials and Processes, Bibliothekstraße 1, 28359 Bremen, Germany
,
Sven Schultzke 
a   University of Bremen, Institute for Analytical and Organic Chemistry, Leobener Straße 7, 28359 Bremen, Germany
b   MAPEX Center for Materials and Processes, Bibliothekstraße 1, 28359 Bremen, Germany
,
Souvik Ghosh 
a   University of Bremen, Institute for Analytical and Organic Chemistry, Leobener Straße 7, 28359 Bremen, Germany
b   MAPEX Center for Materials and Processes, Bibliothekstraße 1, 28359 Bremen, Germany
,
Anne Staubitz  ∗
a   University of Bremen, Institute for Analytical and Organic Chemistry, Leobener Straße 7, 28359 Bremen, Germany
b   MAPEX Center for Materials and Processes, Bibliothekstraße 1, 28359 Bremen, Germany
› Author AffiliationsA.S. and S.S. thank the German Research Foundation (DFG) for the financial support within the priority program SPP 2100 ‘Soft Material Robotic Systems’, Subproject STA1195/5-1, ‘Insect feet inspired concepts soft touch grippers with dynamically adjustable grip strength’.
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Abstract

Azobenzenes are among the most extensively used molecular switches for many different applications. The need to tailor them to the required task often requires further functionalization. Cross-coupling reactions are ideally suited for late-stage modifications. This review provides an overview of recent developments in the modification of azobenzene and its derivatives by cross-coupling reactions.

1 Introduction

2 Azobenzenes as Formally Electrophilic Components

2.1 Palladium Catalysis

2.2 Nickel Catalysis

2.3 Copper Catalysis

2.4 Cobalt Catalysis

3 Azobenzenes as Formally Nucleophilic Components

3.1 Palladium Catalysis

3.2 Copper Catalysis

3.3 C–H Activation Reactions

4 Azobenzenes as Ligands in Catalysts

5 Diazocines

5.1 Synthesis

5.2 Cross-Coupling Reactions

6 Conclusion

Key words

azobenzene - diazocine - molecular switches - cross-coupling reactions - C–H activation - metal-catalyzed


Publication History

Received: 07 October 2020

Accepted after revision: 19 November 2020

Article published online:
28 January 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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