Abstract

This review presents the most recent developments on the synthesis of dipyrromethanes, covering classical synthetic strategies, using acid catalyzed condensation of pyrroles and aldehydes or ketones, and recent breakthroughs which allow the synthesis of these type of heterocycles with new substitution patterns.

Highlights

  • Dipyrromethanes are well known synthetic scaffolds for the synthesis of macrocycles and dipyrromethene metal complexes

  • Dipyrromethanes occupy a central place in porphyrin chemistry

  • The dipyrromethane structures employed in the synthesis of naturally occurring porphyrins typically bear substituents at the β-positions and lack any substituent at the meso-position

Read more

Summary

Introduction

Dipyrromethanes are well known synthetic scaffolds for the synthesis of macrocycles and dipyrromethene metal complexes. The dipyrromethanes with substituents at the meso-position have come to play a valuable role in the preparation of synthetic porphyrins [1,2], calixpyrroles [3], chlorins [4], corroles [5], and expanded porphyrins, namely saphyrins and smaragdyrins [6,7] (Figure 1). The synthetic strategies have been organized in two main approaches: classical synthetic strategies based on the first report on the synthesis of meso-substituted dipyrromethanes, disclosed in 1974 [33], using acid catalyzed condensation of pyrrole and aldehydes; and recent breakthroughs in dipyrromethane chemistry which allow the synthesis of dipyrromethanes with new substitution patterns

Hydrochloric Acid-Catalyzed Dipyrromethane Synthesis
Synthesisderivatives of dipyrromethanes
Trifluoroacetic Acid-Catalyzed Dipyrromethane Synthesis
Dipyrromethanes
Dipyrromethane
11. Synthesis
Boron Trifluoride Diethyl Etherate-Catalyzed Dipyrromethane Synthesis
15. InCl synthesis of triptycenyldipyrromethane
Other Strategies
17. Synthesis
18. Synthesis of2B meso-trifluoromethyldipyrromethanes
21. Synthesis
O Methods
29. Synthesis
30. Synthesis
Findings
Conclusions

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call

Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.