Decarboxylative Alkylation of Carboxylic Acids with Easily Oxidizable Functional Groups Catalyzed by an Imidazole‐Coordinated Fe<sub>3</sub> Cluster under Visible Light Irradiation

Decarboxylative alkylation of carboxylic acids with easily oxidizable functional groups such as phenol and indole functionalities was achieved using a catalytic amount of basic iron(III) acetate, Fe(OAc)<sub>2</sub>(OH), in the presence of benzimidazole under 427 nm LED irradiation. Kinetic analyses of this catalytic reaction revealed that the reaction rate is first-order in alkenes and is linearly correlated with the light intensity; the faster reaction rate for the benzimidazole-ligated species was consistent with the increased absorbance in the visible light region. Wide functional group tolerance for the easily oxidizable groups is ascribed to the weak oxidation ability of the in situ-generated oxo-bridged iron clusters compared with other iron(III) species.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-09-03
DOI
https://doi.org/10.1002/chem.202402705
Citations
8
Primary Topic
Metal-Catalyzed Oxygenation Mechanisms
Type
article
Field-Weighted Citation Impact
1.27

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article

Decarboxylative Alkylation of Carboxylic Acids with Easily Oxidizable Functional Groups Catalyzed by an Imidazole‐Coordinated Fe3 Cluster under Visible Light Irradiation

Tetsuro Kusamoto, Hayato Tsurugi, Sota Tamaki
8 citations
Chemistry - A European Journal
Metal-Catalyzed Oxygenation Mechanisms
1.27
article

Decarboxylative Alkylation of Carboxylic Acids with Easily Oxidizable Functional Groups Catalyzed by an Imidazole‐Coordinated Fe3 Cluster under Visible Light Irradiation

Tetsuro Kusamoto, Hayato Tsurugi, Sota Tamaki
article en
8 citations

Abstract

Decarboxylative alkylation of carboxylic acids with easily oxidizable functional groups such as phenol and indole functionalities was achieved using a catalytic amount of basic iron(III) acetate, Fe(OAc)<sub>2</sub>(OH), in the presence of benzimidazole under 427 nm LED irradiation. Kinetic analyses of this catalytic reaction revealed that the reaction rate is first-order in alkenes and is linearly correlated with the light intensity; the faster reaction rate for the benzimidazole-ligated species was consistent with the increased absorbance in the visible light region. Wide functional group tolerance for the easily oxidizable groups is ascribed to the weak oxidation ability of the in situ-generated oxo-bridged iron clusters compared with other iron(III) species.

Chemistry - A European JournalVol. 30(69)
Osaka Gakuin University (JP), Osaka University of Economics (JP), The University of Osaka (JP)
Hosokawa Powder Technology Foundation, Japan Society for the Promotion of Science
Openalex Percentile: Top 22%
Metal-Catalyzed Oxygenation Mechanisms
1.27
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