Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Abstract

Multiply arylated heterocycles are interesting structures with highly useful functions and fascinating optoelectronic and biological properties. Pyridines are an important class of compounds, playing a role in various fields of chemistry. When the pyridine ring is connected to other aromatic systems, novel stereochemical outcomes may arise. This work summarizes different methodologies applied for the synthesis of substituted arylpyridine derivatives and summarizes stereochemical phenomena resulting from atropisomerism present in certain arylated pyridines.

1 Introduction

2 Arylpyridines Containing meta- and para-Substituted Phenyl Groups

2.1 Arylpyridine Derivatives as Amphetamine Analogues Markers

2.2 Site-Selective Synthesis of Arylpyridines

3 Atropisomerism in Arylpyridines Containing ortho-Substituted Phenyl Groups

3.1 Synthesis of Arylpyridines Containing ortho-Substituted Phenyl Groups

3.2 Other Methods for the Preparation of Arylated Pyridines

4 Fully Substituted Pyridine Derivatives

4.1 Site-Selective Synthesis of Fully Arylated Pyridines

4.3 Atropisomerism in Densely Substituted Arylpyridines Containing ortho-Substituted Phenyl Groups

5 Enantioselective Synthesis of Arylpyridine Derivatives

6 Conclusion

Key words

pyridine derivatives - heterocyclic compounds - stereochemistry - atropisomerism - Suzuki–Miyaura reaction

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