Light‐Triggered Nickel‐Catalyzed Azide−Alkyne Cycloaddition for the Preparation of 1,5‐Disubstituted 1,2,3‐Triazoles

When irradiated by UVA, a Ni(II) precatalyst integrating a benzophenone chromophore in its structure catalyzes the regioselective cycloaddition of alkynes and azides to produce 1,5‐disubsituted 1,2,3‐triazoles with 1,5:1,4 regioisomer ratios ranging from 1.7:1 to >20:1. Speciation and reactivity...

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Veröffentlicht in:Advanced synthesis & catalysis 2022-12, Vol.364 (24), p.4266-4270
Hauptverfasser: Abadie, Baptiste, Almansa, Axel, He, Ouchan, Massip, Stéphane, Molton, Florian, Duboc, Carole, Vincent, Jean‐Marc
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Sprache:eng
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Zusammenfassung:When irradiated by UVA, a Ni(II) precatalyst integrating a benzophenone chromophore in its structure catalyzes the regioselective cycloaddition of alkynes and azides to produce 1,5‐disubsituted 1,2,3‐triazoles with 1,5:1,4 regioisomer ratios ranging from 1.7:1 to >20:1. Speciation and reactivity studies revealed that the reaction most likely proceeds through a Ni(I)/Ni(III) catalytic cycle.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201026