Preparation of Carbazoles Involving 6π-Electrocyclization, Photoredox-, Electrochemical-, and Thermal Cyclization Reactions: Mechanistic Insights

Carbazole is a heterocyclic motif that can be found in a diverse array of natural and unnatural products displaying a wide range of biological and physiological properties. Furthermore, this heterocycle is part of electronic materials like photoconducting polymers and organic optoelectronic materials owing to its excellent photophysical characteristics. Consequently, the development of synthetic strategies for carbazole scaffolds holds potential significance in biological and material fields. In this regard, a variety of preparation methods has been developed to exploit their efficient and distinct formation of new C-C and C-heteroatom bonds under mild conditions and enabling broad substrate diversity and functional group tolerance. Therefore, this review focuses on the synthesis of a set of carbazole derivatives describing a variety of methodologies that involve direct irradiation, photosensitization, photoredox, electrochemical and thermal cyclization reactions. Synthetic methods for the preparation of the carbazole moiety are reviewed. These methods describe the formation of new C-C and C-N bonds under mild conditions enabling broad substrate diversity and functional group tolerance. Photochemical, thermal and electrochemical transformations are described as interesting preparative methodologies.image

Automated summary

This review focuses on the synthesis of carbazole derivatives using various methods, such as direct irradiation, photosensitization, photoredox, electrochemical, and thermal cyclization reactions. The methods described in this review enable efficient formation of new C-C and C-heteroatom bonds under mild conditions and allow for broad substrate diversity and functional group tolerance.