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

ABSTRACT: 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)]₂ 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)]₂ was performed on the bench to furnish the pure tetrahydropyridine product in 93% yield.

SUBMITTER: Mesganaw T 

PROVIDER: S-EPMC4183668 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature