Citation: Christine Tran, Aïcha Abdallah, Valentin Duchemann, Guillaume Lefèvre, Abdallah Hamze. Iron-catalyzed reductive cyclization of nitroarenes: Synthesis of aza-heterocycles and DFT calculations[J]. Chinese Chemical Letters, ;2023, 34(3): 107758. doi: 10.1016/j.cclet.2022.107758 shu

Iron-catalyzed reductive cyclization of nitroarenes: Synthesis of aza-heterocycles and DFT calculations

a.
CNRS, BioCIS, Université Paris-Saclay, Châtenay-Malabry 92290, France
b.
Chimie ParisTech, CNRS, Institute of Chemistry for Life and Health Sciences, PSL University, CSB2D, Paris 75005, France

christine.tran@universite-paris-saclay.fr

guillaume.lefevre@chimieparistech.psl.eu

abdallah.hamze@universiteparis-saclay.fr

Received Date: 17 June 2022
Revised Date: 11 August 2022
Accepted Date: 16 August 2022
Available Online: 18 August 2022

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Research into environmentally friendly strategies for hydrogen transfer reduction is increasing, along with the need for more elaborate heterocyclic platforms. Within this context, we develop a new approach for substituted dihydrobenzo[c]carbazoles and indoles. These compounds were synthesized through an iron-catalyzed hydrogen transfer reduction of nitroarenes, followed by intramolecular cyclization. This transformation involves using a Knölker-type catalyst, Cs₂CO₃ as the base, and benzyl alcohol as the non-expensive and low volatile hydrogen donor. We synthesize 30 examples of aza-heterocycles with moderate to excellent yields by applying this strategy. Additionally, DFT calculations demonstrated that the pathway reaction could follow an anionic mechanism.
- Iron,
- Cyclization,
- Nitroarenes,
- Dihydrobenzo[c]carbazoles,
- Indoles
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