Eco-friendly and efficient Friedel–Crafts acylation of activated arenes catalyzed with low-loaded ferric chloride in propylene carbonate as the solvent: scope and mechanistic insights

The Friedel-Crafts acylation of arenes is a fundamental reaction extensively employed in both academic research and industrial applications. A significant limitation of this reaction is the requirement for stoichiometric amounts of Lewis acid catalysts, which are typically sensitive and generate considerable waste. In this study, we present an improved catalytic approach for the Friedel-Crafts acylation of activated arenes. Using acyl chlorides and acid anhydrides as acylating agents, the reaction is efficiently catalyzed by 5 mol% iron(iii) chloride in propylene carbonate, an environmentally friendly solvent that outperforms traditional solvents in maintaining high reaction efficiency under catalytic conditions. This green methodology demonstrates high effectiveness and broad applicability, yielding aromatic ketones in good to excellent yields. Preliminary DFT calculations were carried out to rationalize the mechanism of the reaction.

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Publication Details

Journal
RSC Advances
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ra03638k
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Eco-friendly and efficient Friedel–Crafts acylation of activated arenes catalyzed with low-loaded ferric chloride in propylene carbonate as the solvent: scope and mechanistic insights

Jamil Kraı̈em, Marie Fustier‐Boutignon, Sami Lakhdar, Saïf Eddine Chérif et al.
RSC Advances
Carbon dioxide utilization in catalysis
article

Eco-friendly and efficient Friedel–Crafts acylation of activated arenes catalyzed with low-loaded ferric chloride in propylene carbonate as the solvent: scope and mechanistic insights

Jamil Kraı̈em, Marie Fustier‐Boutignon, Sami Lakhdar, Saïf Eddine Chérif, Mayssa Chehaibi, Rafif Raddadi
article en

Abstract

The Friedel-Crafts acylation of arenes is a fundamental reaction extensively employed in both academic research and industrial applications. A significant limitation of this reaction is the requirement for stoichiometric amounts of Lewis acid catalysts, which are typically sensitive and generate considerable waste. In this study, we present an improved catalytic approach for the Friedel-Crafts acylation of activated arenes. Using acyl chlorides and acid anhydrides as acylating agents, the reaction is efficiently catalyzed by 5 mol% iron(iii) chloride in propylene carbonate, an environmentally friendly solvent that outperforms traditional solvents in maintaining high reaction efficiency under catalytic conditions. This green methodology demonstrates high effectiveness and broad applicability, yielding aromatic ketones in good to excellent yields. Preliminary DFT calculations were carried out to rationalize the mechanism of the reaction.

RSC AdvancesVol. 15(38)
Centre National de la Recherche Scientifique (FR), Université Toulouse III - Paul Sabatier (FR), University of Monastir (TN), Laboratoire Hétérochimie Fondamentale et Appliquée (FR)
Ministère de l’Enseignement Supérieur et de la Recherche Scientifique, Agence Nationale de la Recherche, Centre National de la Recherche Scientifique
Openalex Percentile: Top 83%
Carbon dioxide utilization in catalysis
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Eco-friendly and efficient Friedel–Crafts acylation of activated arenes catalyzed with low-loaded ferric chloride in propylene carbonate as the solvent: scope and mechanistic insights — Jamil Kraı̈em, Marie Fustier‐Boutignon, et al. · RSC Advances (2025) | TGRS Research Map | TGRS