Cross-Coupling Reactions of Polyhalogenated Heterocycles

Peter Langer

doi:10.1055/s-0040-1719906

Synlett, Table of Contents

Synlett 2022; 33(11): 1029-1051
DOI: 10.1055/s-0040-1719906

account

Cross-Coupling Reactions of Polyhalogenated Heterocycles

Authors

Peter Langer ∗

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany URL: http://www.langer.chemie.uni-rostock.de/

^bLeibniz-Institut für Katalyse an der Universität Rostock e. V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Abstract

All articles of this category

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

Full Text

References

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