Iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light

Fall, Arona; Magdei, Mihaela; Savchuk, Mariia; Oudeyer, Sylvain; Beucher, Hélène; Brière, Jean-François

doi:10.1039/d4cc01766h

Chem. Commun.

2024

DOI: 10.1039/d4cc01766h

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Iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light

Arona Fall,

Mihaela Magdei,

Mariia Savchuk

et al.

Abstract: Herein, we disclose an eco-efficient redox-neutral iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light (427 nm) giving cyclic hydrazine derivatives with dr ranging from 82:18 to >96:4....

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Cited by 5 publications

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

Tamaki,

Kusamoto,

Tsurugi

2024

Chemistry A European J

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

Tamaki,

Kusamoto,

Tsurugi

2024

Chemistry A European J

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Light‐Mediated Radical Addition to Azomethine Compounds: Novel Reactivity and Activation Modes

Rubanov,

Levin,

Dilman

2024

The Chemical Record

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Azomethines is a class of compounds, which have traditionally served as electrophilic substrates, but their reactions with radicals have long been limited. Photocatalysis provided ample opportunities for promoting these reactions, with wide variety of reagents serving as precursors of radicals. Besides regular addition mode at the azomethine fragment, the oxidative pathway, in which the C=N bond remains in the product, has become possible by proper selection of redox catalyst. This review summarizes new developments in this rapidly developing field over the past five years. New concepts on activation of the C=N bond towards radical attack are discussed.

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Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids

Golagani,

Prakash,

Thapa

et al. 2024

Org. Lett.

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A novel photoinduced Fe(OTf)2/2,4,6-collidine-catalyzed alkylation of Morita–Baylis–Hillman (MBH) acetates using carboxylic acids in a regio- and stereoselective manner is reported. This method demonstrates a broad scope, encompassing various carboxylic acids and MBH acetates, including drugs and bioactive molecules, to synthesize densely functionalized cinnamates and acrylates. The reactions are performed in the green solvent dimethyl carbonate under oxidant-free conditions. Based on control experiments, a plausible mechanism involving an Fe(II)–Fe(III)–Fe(II) cycle is proposed.

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Iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light

Abstract: Herein, we disclose an eco-efficient redox-neutral iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light (427 nm) giving cyclic hydrazine derivatives with dr ranging from 82:18 to >96:4....

Cited by 5 publications

References 47 publications

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

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

Light‐Mediated Radical Addition to Azomethine Compounds: Novel Reactivity and Activation Modes

Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids

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Iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light

Abstract: Herein, we disclose an eco-efficient redox-neutral iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light (427 nm) giving cyclic hydrazine derivatives with dr ranging from 82:18 to >96:4....

Cited by 5 publications

References 47 publications

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

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

Light‐Mediated Radical Addition to Azomethine Compounds: Novel Reactivity and Activation Modes

Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids

Contact Info

Product

Resources

About

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

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