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Direct Arylation of Unactivated Arenes Using Earth-Abundant Iron/Tetra-Aza Macrocyclic Complexes
Tahmina Afroz1, David M Freire1, Timothy J Hubin2
1Texas Christian University, Department of Chemistry and Biochemistry, Fort Worth, Texas 76048, United States.
Inorganic Chemistry
|January 28, 2026
Summary
Iron catalysts offer a sustainable alternative to palladium for synthesizing biaryl compounds. This study demonstrates iron(II) complexes efficiently catalyze direct arylation of pyrrole, achieving high yields and broad substrate scope for greener drug discovery.
Area of Science:
- Organic Chemistry
- Catalysis
- Medicinal Chemistry
Background:
- Biaryl motifs are crucial in pharmaceutical development.
- Palladium-catalyzed cross-coupling methods face sustainability and cost challenges.
Purpose of the Study:
- To explore iron(II) complexes as a greener alternative to palladium for C-C bond formation.
- To develop a sustainable catalytic system for direct arylation of pyrrole.
Main Methods:
- Utilized iron(II) complexes with tetra-aza macrocyclic ligands (Me2Cyclam, L1).
- Performed direct arylation of pyrrole with phenylboronic acids under aerobic conditions.
- Conducted mechanistic studies including DFT analysis.
Main Results:
- Optimized [Fe2+L1(Cl)2] complex achieved up to 66% yield with broad substrate compatibility (23 derivatives).
- Demonstrated excellent functional group tolerance (halides, esters, electron-deficient substituents).
- Identified meta-substitution and mild electron-withdrawing effects as favorable for reactivity.
Conclusions:
- Iron catalysts offer a sustainable and cost-effective platform for C-C bond formation.
- Iron(III)-hydroperoxo species are suggested as the operative oxidant.
- DFT analysis indicated enhanced boron electrophilicity promotes the transmetalation step.
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