A new imine ligand avoiding imine–enamine rearrangement and cyclometallation: Synthesis and coordination of Me3C6H2CH2NCHtBu

During the hydrogenation of oximes, the temporary protection of the nitrogen moiety by a hydroxyl group promises to provide access to a highly selective synthetic route to primary amines. We will show that the reaction, however, proceeds via the more general network of imine and Schiff base chemistry. By choosing the right catalyst and conditions, specific pathways can be selected enabling us to steer the route from a pool of intermediate compounds to either primary or secondary amines. Thus, nickel catalysts provide high selectivity towards primary amines albeit at a moderate activity, while noble metal catalysts show good selectivity towards secondary amines, as well as high activity. Detailed analysis of the reaction sequence over Ni/SiO₂ provides insight into the pathways and provides understanding for the tools to obtain outstanding selectivities in the hydrogenation of oximes and other amine precursors

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A new imine ligand avoiding imine–enamine rearrangement and cyclometallation: Synthesis and coordination of Me3C6H2CH2NCHtBu

Cited by 2 publications

References 15 publications

Syntheses, characterization, solution behavior and catalytic activity of trans-[(guanidine)2PdX2] (X = Cl and OC(O)R; R = Me, Ph and Bu) in Heck–Mizoroki coupling reactions involving chloroarenes/methyl acrylate

Syntheses, characterization, solution behavior and catalytic activity of trans-[(guanidine)2PdX2] (X = Cl and OC(O)R; R = Me, Ph and Bu) in Heck–Mizoroki coupling reactions involving chloroarenes/methyl acrylate

Controlling selectivity in the reaction network of aldoxime hydrogenation to primary amines

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A new imine ligand avoiding imine–enamine rearrangement and cyclometallation: Synthesis and coordination of Me3C6H2CH2NCHtBu

Cited by 2 publications

References 15 publications

Syntheses, characterization, solution behavior and catalytic activity of trans-[(guanidine)2PdX2] (X = Cl and OC(O)R; R = Me, Ph and Bu) in Heck–Mizoroki coupling reactions involving chloroarenes/methyl acrylate

Syntheses, characterization, solution behavior and catalytic activity of trans-[(guanidine)2PdX2] (X = Cl and OC(O)R; R = Me, Ph and Bu) in Heck–Mizoroki coupling reactions involving chloroarenes/methyl acrylate

Controlling selectivity in the reaction network of aldoxime hydrogenation to primary amines

Contact Info

Product

Resources

About

Syntheses, characterization, solution behavior and catalytic activity of trans-[(guanidine)2PdX2] (X = Cl and OC(O)R; R = Me, Ph and Bu) in Heck–Mizoroki coupling reactions involving chloroarenes/methyl acrylate

Syntheses, characterization, solution behavior and catalytic activity of trans-[(guanidine)2PdX2] (X = Cl and OC(O)R; R = Me, Ph and Bu) in Heck–Mizoroki coupling reactions involving chloroarenes/methyl acrylate