Preparative Synthesis of Highly Substituted Tetrahydropyridines via a Rh(I)-Catalyzed C–H Functionalization Sequence


We report a Rh­(I)-catalyzed C–H activation/alkenylation/electrocyclization cascade and subsequent reduction for the synthesis of highly substituted tetrahydropyridines. These products can be accessed on a gram scale with low catalyst loadings and at high reaction concentrations. Additionally, a modified Rh-catalyst, prepared from [RhCl­(cod)]<sub>2</sub> as a robust bench-stable precatalyst was developed to enable straightforward reaction set up without the use of a glovebox. To demonstrate the practicality of this reaction, a >100 mmol scale Rh-catalyzed cascade reaction sequence utilizing the air-stable precatalyst [RhCl­(cod)]<sub>2</sub> was performed on the bench to furnish the pure tetrahydropyridine product in 93% yield

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oaioai:figshare.com:article/2040498Last time updated on 2/12/2018

This paper was published in FigShare.

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