Hydride-free reduction of propargyl electrophiles: a nickel-catalyzed photoredox strategy for allene synthesis

Hu, Tingjun; Fagué, Vincent; Bouyssi, Didier; Monteiro, Nuno; Amgoune, Abderrahmane

doi:10.1039/d4gc00984c

Green Chem.

2024

DOI: 10.1039/d4gc00984c

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Hydride-free reduction of propargyl electrophiles: a nickel-catalyzed photoredox strategy for allene synthesis

Tingjun Hu,

Vincent Fagué,

Didier Bouyssi

et al.

Abstract: Herein we report a catalytic reduction of propargyl carbonates to allenes mediated by nickel molecular catalyst. The catalytic system use light as driving force and amine as the sole hydrogen...

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Nickel-Catalyzed Photoredox Allenylation of Alkyl Halides

Hu,

Beluze,

Fagué

et al. 2024

Org. Lett.

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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 S N 2 ′ oxidative addition at Ni(I) with silyl radicalinduced 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.

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Nickel-Catalyzed Photoredox Allenylation of Alkyl Halides

Hu,

Beluze,

Fagué

et al. 2024

Org. Lett.

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Hydride-free reduction of propargyl electrophiles: a nickel-catalyzed photoredox strategy for allene synthesis

Abstract: Herein we report a catalytic reduction of propargyl carbonates to allenes mediated by nickel molecular catalyst. The catalytic system use light as driving force and amine as the sole hydrogen...

Cited by 1 publication

References 48 publications

Nickel-Catalyzed Photoredox Allenylation of Alkyl Halides

Nickel-Catalyzed Photoredox Allenylation of Alkyl Halides

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