Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BF3 Complexes: A Modular Route to Functionalized Azacycles

Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range of cyclic imine-BF3 complexes to provide α-functionalized azacycles in an operationally simple process. A three-component variant of this transformation incorporating [1...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2024-09
Main Authors: Bhatt, Kamal, Adili, Alafate, Tran, Andrew H, Elmallah, Kamal M, Ghiviriga, Ion, Seidel, Daniel
Format: Article
Language:English
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Summary:Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range of cyclic imine-BF3 complexes to provide α-functionalized azacycles in an operationally simple process. A three-component variant of this transformation incorporating [1.1.1]propellane as an additional reaction partner enables the synthesis of valuable bicyclopentane (BCP)-containing azacycles. Reactions exhibit good functional group compatibility, enabling late-stage modification of complex bioactive molecules.Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range of cyclic imine-BF3 complexes to provide α-functionalized azacycles in an operationally simple process. A three-component variant of this transformation incorporating [1.1.1]propellane as an additional reaction partner enables the synthesis of valuable bicyclopentane (BCP)-containing azacycles. Reactions exhibit good functional group compatibility, enabling late-stage modification of complex bioactive molecules.
ISSN:1520-5126
1520-5126
DOI:10.1021/jacs.4c08754