op500225c_si_001.pdf (1.7 MB)
Preparative Synthesis of Highly Substituted Tetrahydropyridines via a Rh(I)-Catalyzed C–H Functionalization Sequence
journal contribution
posted on 2015-12-17, 04:41 authored by Tehetena Mesganaw, Jonathan A. EllmanWe
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.