Cross-Coupling Reactions of Polyhalogenated Heterocycles

In memoriam of Prof. Dr. Tamás Patonay

Abstract

Palladium-catalyzed cross-coupling reactions of polyhalogenated heterocycles provide a convenient access to multifold arylated and alkynylated ring systems with a broad spectrum of physical and medicinal properties. Products include thiophenes, selenophenes, pyrroles, indoles, furans, benzofurans, pyrazoles, pyridines, quinolines, pyrimidines, pyrazines, naphthyridines, quinoxalines, and others. The regioselectivity of the coupling reactions is controlled by a combination of electronic and steric parameters. While a number of couplings can be carried out essentially under standard conditions, others require the use of more sophisticated ligands and a thorough optimization of the conditions, such as solvent, temperature, or reaction time. The present Account provides a personalized overview of coupling reactions of polyhalogenated heterocycles.

1 Introduction

2 Thiophenes

3 Selenophenes

4 Pyrroles and Indoles

5 Furans and Benzofurans

6 Pyrazoles

7 Pyridines

8 Quinolines

9 Pyrimidines and Pyrazines

10 Naphthyridines and Quinoxalines

11 Miscellaneous

12 Conclusions

Keywords

catalysis - cross-coupling - heterocycles - palladium - regioselectivity

Publication History

Received: 31 January 2022

Accepted: 08 February 2022

Article published online:
24 March 2022

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