ArticleChemical science2024
Addition of allyl Grignard to nitriles in air and at room temperature: experimental and computational mechanistic insights in pH-switchable synthesis.
Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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5 authors at 3 institutions in 1 country.
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Abstract
A straightforward and selective conversion of nitriles into highly substituted tetrahydropyridines, aminoketones or enamines by using allylmagnesium bromide as an addition partner (under neat conditions) and subsequent treatment with different aqueous-based hydrolysis protocols is reported. Refuting the conventional wisdom of the incompatibility of Grignard reagents with air and moisture, we herein report that the presence of water allows us to promote the chemoselective formation of the target tetrahydropyridines over other competing products (even in the case of highly challenging aliphatic nitriles). Moreover, the careful tuning of both the reaction media employed (acid or basic aqueous solutions for the hydrolysis protocol) and the electronic properties of the starting nitriles allowed us to design a multi-task system capable of producing either β-aminoketones or enamines in a totally selective manner. Importantly, and for the first time in the chemistry of main-group polar organometallic reagents in non-conventional protic solvents (
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