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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Veröffentlicht in:	Journal of the American Chemical Society 2024-09, Vol.146 (38), p.26331-26339
Hauptverfasser:	Bhatt, Kamal, Adili, Alafate, Tran, Andrew H., Elmallah, Kamal M., Ghiviriga, Ion, Seidel, Daniel
Format:	Artikel
Sprache:	eng
Schlagworte:	alkylation decarboxylation feedstocks photocatalysis
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description	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.
doi_str_mv	10.1021/jacs.4c08754
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subjects	alkylation decarboxylation feedstocks photocatalysis
title	Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF3 Complexes: A Modular Route to Functionalized Azacycles
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