Three-Component Coupling Synthesis of Diversely Substituted N-Aryl Pyrroles Catalyzed by Iron(III) Chloride

Abstract

An efficient and operationally simple three-component coupling synthesis of varieties of N-aryl substituted pyrroles is described in the presence of sustainable and environmentally benign metal catalyst, FeCl₃. This method provides a straightforward approach for the synthesis of N-aryl substituted pyrroles in good yields from easily accessible starting materials such as nitroalkenes, 1,3-dicarbonyl compounds, and primary aromatic amines. The reaction proceeds through a catalytic sequence of Fe(III)-catalyzed amination/Michael/cycloisomerization reactions.

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GRAPHICAL ABSTRACT

Keywords:

• Iron
• multicomponent
• N-aryl pyrrole
• sustainable
• tandem

ACKNOWLEDGMENTS

We gratefully acknowledge the financial and infrastructural support from the University Grants Commission (UGC)–CAS program of the Department of Chemistry, Jadavpur University. The Department of Science and Technology (DST)–PURSE program is also gratefully acknowledged. S. S. and K. B. are thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for their fellowships. S. M. and S. B. are also thankful to the UGC, New Delhi, Jadavpur University, New Delhi, India, respectively, for their fellowships.

Notes

^a All reactions were carried out using nitroalkene (1 mmol), 1,3-dicarbonyl compounds (1 mmol), and aromatic amines (1.5 mmol) with solvent (1 mL).

^b Yield obtained after column chromatography.

^a All reactions were carried out using nitroalkene (1 mmol), 1,3-dicarbonyl compounds (1 mmol), and aromatic amines (1.5 mmol) in nitromethane (1 mL) at 100 °C.

^b Yield obtained after column chromatography.