Functionalization of the Imidazole Backbone by Means of a Tailored and Optimized Oxidative Heck Cross-Coupling
Journal article, Peer reviewed
Published version
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Åpne
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https://hdl.handle.net/11250/2763117Utgivelsesdato
2020Metadata
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- Department of Chemistry [442]
- Registrations from Cristin [10237]
Sammendrag
A general and selective Pd-catalyzed cross-coupling of aromatic boronic acids with vinyl-imidazoles is disclosed. Unlike most cross-coupling reactions, this method operates well in absence of bases avoiding the formation of by-products. The reactivity is highly enhanced by the presence of nitrogen-based ligands, in particular bathocuproine. The method involves MnO2 as oxidant for the oxidation Pd (0)→Pd (II), a much weaker oxidant than previously reported in the literature. This allows for the use of reactants that possess a multitude of functional groups. A scope and limitation study involving a series of 24 boronic acids, whereof 18 afforded TMs in yields in the range 41–95%. The disclosed method constitutes the first general method for the oxidative Heck cross-coupling on the imidazole scaffold, which moreover operates with a selection of other heterocycles.