Nickel-Catalyzed Photoredox Allenylation of Alkyl Halides

We report a dual Ni/photoredox-catalyzed cross-coupling method for propargyl carbonates and nonactivated alkyl bromides, facilitating the synthesis of a variety of substituted allenes under mild and practical conditions. Mechanistically, the reaction integrates Ni-catalyzed activation of the proparg...

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Bibliographic Details
Published in:Organic letters 2024-11, Vol.26 (44), p.9519-9524
Main Authors: Hu, Tingjun, Beluze, Camille, Fagué, Vincent, Kambire, Oho Eliantine, Bouyssi, Didier, Monteiro, Nuno, Amgoune, Abderrahmane
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
cross-coupling reactions
derivatization
Lewis acids
Organic chemistry
redox reactions
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Summary:We report a dual Ni/photoredox-catalyzed cross-coupling method for propargyl carbonates and nonactivated alkyl bromides, facilitating the synthesis of a variety of substituted allenes under mild and practical conditions. Mechanistically, the reaction integrates Ni-catalyzed activation of the propargyl electrophile via SN 2′ oxidative addition at Ni­(I) with silyl radical-induced activation of the alkyl halide through halogen-atom transfer. This methodology provides a gentle approach for introducing allenyl groups into complex halogenated aliphatic molecules, offering further opportunities for derivatization.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03512