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DOI: 10.1055/a-2601-4894
Photoinduced Nickel-Catalyzed 1,2-Acylcyanation of Styrenes with Acyl Fluorides and Trimethylsilyl Cyanide
1,2-Acylcyanation of Styrenes by Photoinduced Nickel Catalysis to Generate Acyl Radicals from Acyl Fluorides.
Org. Lett. 2025;
27: 3361-3367
DOI: 10.1021/acs.orglett.5c00761
Keywords
acylcyanation - acyl fluorides - acyl radicals - nickel catalysis - photocatalysis - styrenes
Significance
Miura and co-workers report a photoinduced nickel-catalyzed protocol for the 1,2-acylcyanation of styrene derivatives with acyl fluorides and trimethylsilyl cyanide. In this three-component transformation, the nickel complex acts as both the visible-light-harvesting photocatalyst and as the transition-metal catalyst for the cross-coupling, thus removing the need for the use of an exogenous photoredox catalyst.
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Comment
The reaction was completely inhibited by the addition of TEMPO, indicating the involvement of radicals in the mechanism. In addition, radical-clock experiments revealed that the transiently generated benzoyl radical reacts with the styrene to form a benzylic radical intermediate. These results, along with further radical trapping experiments, support the shown proposed catalytic cycle.
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Publication History
Article published online:
23 June 2025
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